Benzene Derivatives: The Tanino-Miyashita Synthesis of Zoanthenol

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Benzoic Acid ◽  
University Of Pennsylvania ◽  
University Of Southern California ◽  
Aryl Chlorides ◽  
National University ◽  
Rh Catalyst ◽  
Nitro Aromatics ◽  
La Jolla ◽  
University Of Oslo ◽  
The University

Yuqing Hou of Southern Illinois University found (J. Org. Chem. 2009, 74, 6362) that the peroxy ether 2 served effectively to directly transfer a methoxy group to the lithiated 1 to give 3. Wanzhi Chen of Zhejiang University, Xixi Campus, showed (J. Org. Chem. 2009, 74, 7203) that pyrimidines such as 4, readily prepared from the corresponding phenol, underwent smooth Pd-catalyzed ortho acetoxylation. Trond Vidar Hansen of the University of Oslo observed (Tetrahedron Lett. 2009, 50, 6339) that simple electrophilic formylation of phenols such as 6 also proceeded with high ortho selectivity. Kyung Woon Jung of the University of Southern California optimized (J. Org. Chem. 2009, 74, 6231) the Rh catalyst for ortho C-H insertion, converting 8 into 9. Jin-Quan Yu of Scripps/La Jolla devised (Science 2010, 327, 315) a protocol for carboxy-directed catalytic ortho palladation that allowed subsequent Heck coupling, transforming 10 into 11. Norikazu Miyoshi of the University of Tokushima established (Chem. Lett. 2009, 38, 996) that in situ generated strontium alkyls added 1,6 to benzoic acid 13, to give, after mild oxidative workup, the 4-alkyl benzoic acid 15. Amin Zarei of Islamic Azad University showed (Tetrahedron Lett. 2009, 50, 4443) that their previously developed protocol for preparing stable diazonium silica sulfates could be extended to the preparation of an aryl azide such as 17. Stephen L. Buchwald of MIT developed (J. Am. Chem. Soc. 2009, 131, 12898) a Pd-mediated protocol for the conversion of aryl chlorides to the corresponding nitro aromatics. Virgil Percec of the University of Pennsylvania has also reported (Organic Lett. 2009, 11, 4974) the conversion of an aryl chloride to the borane, and Guy C. Lloyd-Jones has described (Angew. Chem. Int. Ed. 2009, 48, 7612) the conversion of phenols to the corresponding thiols. Kwang Ho Song of Korea University and Sunwoo Lee of Chonnam National University demonstrated (J. Org. Chem. 2009, 74, 6358) that the Ni-mediated homologation of aryl halides worked with a variety of primary and secondary formamides. Kwangyong Park of Chung-Ang University observed (J. Org. Chem. 2009, 74, 9566) that Ni catalysts also mediated the coupling of Grignard reagents with the tosylate 22 not in the usual way but with the C-S bond to give 23.

NEWS AND ANNOUNCEMENTS

PEDIATRICS ◽  
1973 ◽  
Vol 51 (2) ◽  
pp. 315-322
Keyword(s):  
Los Angeles ◽  
University Of Pennsylvania ◽  
University Of Southern California ◽  
Helping Professions ◽  
University Policy ◽  
School Of Medicine ◽  
Curriculum Vitae ◽  
Piagetian Theory ◽  
Pertinent Information ◽  
The University

Advertisement of Professorship: In accordance with University policy, the School of Medicine of the University of Pennsylvania invites qualified persons to apply for the position of Professor and Chairman of the Department of Pediatrics. A complete curriculum vitae and bibliography, together with any other pertinent information, should be sent to: Office of the Dean, University of Pennsylvania School of Medicine, Philadelphia, Pennsylvania 19104, for the attention of the Chairman of the Pediatric Search Committee. Conference of Piacetian Theory: The University Affiliated Program at Children's Hospital of Los Angeles and the School of Education of the University of Southern California will sponsor a conference entitled Piagetian Theory: The Helping Professions and the School Age Child on February 16, 1973.

Transition Metal-Mediated Construction of Carbocycles: Dimethyl Gloiosiphone A (Takahashi), Pasteurestin A (Mulzer), and Pentalenene (Fox)

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Transition Metal ◽  
South Florida ◽  
Health Science ◽  
Pt Catalyst ◽  
Max Planck ◽  
Au Catalyst ◽  
Ru Catalyst ◽  
National University ◽  
Rh Catalyst ◽  
The University

There continue to be new developments in transition metal- and lanthanide-mediated construction of carbocycles. Although a great deal has been published on the asymmetric cyclopropanation of styrene, relatively little had been reported for other classes of alkenes. Tae-Jeong Kim of Kyungpook National University has devised (Tetrahedron Lett. 2007, 48, 8014) a Ru catalyst for the cyclopropanation of simple α-olefins such as 1. X. Peter Zhang of the University of South Florida has developed (J. Am.Chem. Soc. 2007, 129, 12074) a Co catalyst for the cyclopropanation of alkenes such as 5 having electron-withdrawing groups. Alexandre Alexakis of the Université de Genève has reported(Angew. Chem. Int. Ed. 2007, 46, 7462) simple monophosphine ligands that enabled enantioselective conjugate addition to prochiral enones, even difficult substrates such as 8. Seunghoon Shin of Hanyang University has found (Organic Lett. 2007, 9, 3539) an Au catalyst that effected the diastereoselective cyclization of 10 to the cyclohexene 11, and Radomir N. Saicic of the University of Belgrade has carried out (Organic Lett. 2007, 9, 5063), via transient enamine formation, the diastereoselective cyclization of 12 to the cyclohexane 13. Alois Fürstner of the Max-Planck- Institut, Mülheim has devised (J. Am. Chem. Soc. 2007, 129, 14836) a Rh catalyst that cyclized the aldehyde 14 to the cycloheptenone 15. Some of the most exciting investigations reported in recent months have been directed toward the direct diastereo- and enantioselective preparation of polycarbocyclic products. Rai-Shung Liu of National Tsing-Hua University has extended (J. Org. Chem. 2007, 72, 567) the intramolecular Pauson-Khand cyclization to the epoxy enyne 16, leading to the 5-5 product 17. Michel R. Gagné of the University of North Carolina has devised (J. Am. Chem. Soc. 2007, 129, 11880) a Pt catalyst that smoothly cyclized the polyene 18 to the 6-6 product 19. Yoshihiro Sato of Hokkaido University and Miwako Mori of the Health Science University of Hokkaido have described (J. Am. Chem. Soc. 2007, 129, 7730) a Ru catalyst for the cyclization of 20 to the 5-6-5 product 21. Each of these processes proceeded with high diastereocontrol.

Establishing Arrays of Stereogenic Centers: The Sato/Chida Synthesis of (-)-Kainic Acid

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Catalyst System ◽  
Allylic Alcohol ◽  
University Of Pennsylvania ◽  
Ni Catalyst ◽  
Max Planck ◽  
Stereogenic Centers ◽  
University College London ◽  
Enantioselective Addition ◽  
La Jolla ◽  
The University

Benjamin List of the Max-Planck-Institut, Mülheim, devised (J. Am. Chem. Soc. 2010, 132, 10227) a catalyst system for the stereocontrolled epoxidation of a trisubstituted alkenyl aldehyde 1. Takashi Ooi of Nagoya University effected (Angew. Chem. Int. Ed. 2010, 49, 7562; see also Org. Lett. 2010, 12, 4070) enantioselective Henry addition to an alkynyl aldehyde 3. Madeleine M. Joullié of the University of Pennsylvania showed (Org. Lett. 2010, 12, 4244) that an amine 7 added selectively to an alkynyl aziridine 6. Yutaka Ukaji and Katsuhiko Inomata of Kanazawa University developed (Chem. Lett. 2010, 39, 1036) the enantioselective dipolar cycloaddition of 9 with 10. K. C. Nicolaou of Scripps/La Jolla observed (Angew. Chem. Int. Ed. 2010, 49, 5875; see also J. Org. Chem. 2010, 75, 8658) that the allylic alcohol from enantioselective reduction of 12 could be hydrogenated with high diastereocontrol. Masamichi Ogasawara and Tamotsu Takahashi of Hokkaido University added (Org. Lett. 2010, 12, 5736) the allene 14 to the acetal 15 with substantial stereocontrol. Helen C. Hailes of University College London investigated (Chem. Comm. 2010, 46, 7608) the enzyme-mediated addition of 18 to racemic 17. Dawei Ma of the Shanghai Institute of Organic Chemistry, in the course of a synthesis of oseltamivir (Tamiflu), accomplished (Angew. Chem. Int. Ed. 2010, 49, 4656) the enantioselective addition of 21 to 20. Shigeki Matsunaga of the University of Tokyo and Masakatsu Shibasaki of the Institute of Microbial Chemistry developed (Org. Lett. 2010, 12, 3246) a Ni catalyst for the enantioselective addition of 23 to 24. Juthanat Kaeobamrung and Jeffrey W. Bode of ETH-Zurich and Marisa C. Kozlowski of the University of Pennsylvania devised (Proc. Natl. Acad. Sci. 2010, 107, 20661) an organocatalyst for the enantioselective addition of 27 to 26. Yihua Zhang of China Pharmaceutical University and Professor Ma effected (Tetrahedron Lett. 2010, 51, 3827) the related addition of 27 to 29. There have been scattered reports on the stereochemical course of the coupling of cyclic secondary organometallics. In a detailed study, Paul Knochel of Ludwig-Maximilians- Universität München showed (Nat. Chem. 2020, 2, 125) that equatorial bond formation dominated, exemplified by the conversion of 31 to 33.

The Little Sycamore Site and the Early Milling Stone Cultures of Southern California

1954 ◽  
Vol 20 (2) ◽  
pp. 112-123 ◽  
Author(s):  
William James Wallace
Keyword(s):  
San Diego ◽  
Southern California ◽  
Coastal Region ◽  
San Diego County ◽  
University Of Southern California ◽  
Santa Barbara ◽  
Field Methods ◽  
Analogous Complex ◽  
La Jolla ◽  
The University

The Presence in the southern California coastal region of prehistoric cultures showing considerable use of milling stones has been recognized for some years. Attention was called to this fact by the publication in 1929 of David Banks Rogers’ Prehistoric Man of the Santa Barbara Coast. Rogers distinguished a sequence of three aboriginal cultures in the Santa Barbara area, the earliest of which (Oak Grove) was characterized by the employment of this form of grinding implement almost to the exclusion of other artifacts. In the same year Malcolm J. Rogers noted a somewhat analogous complex (now La Jolla) in western San Diego County (M. J. Rogers 1929: 456-7). Occurrences of similar assemblages have been reported upon since (Treganza and Malamud 1950; Walker 1952).An investigation conducted at the Little Sycamore site (Ven 1) in Ventura County by a class in archaeological field methods from the University of Southern California uncovered evidence of yet another milling stone complex.

Reactions of Alkenes

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Iron Catalyst ◽  
Catalytic Reduction ◽  
Indian Institute ◽  
Yale University ◽  
Terminal Alkene ◽  
National University ◽  
Institute Of Technology ◽  
La Jolla ◽  
The University

The catalytic reduction of the alkene 1 gave the cis-fused product (not illustrated), by kinetic H₂ addition to the less congested face of the alkene. Ryan A. Shenvi of Scripps La Jolla found (J. Am. Chem. Soc. 2014, 136, 1300) conditions for stepwise HAT, con­verting 1 to the thermodynamically-favored trans-fused ketone 2. Seth B. Herzon of Yale University devised (J. Am. Chem. Soc. 2014, 136, 6884) a protocol for the reduc­tion, mediated by 4, of the double bond of a haloalkene 3 to give the saturated halide 5. The Shenvi conditions also reduced a haloalkene to the saturated halide. Daniel J. Weix of the University of Rochester and Patrick L. Holland, also of Yale University, established (J. Am. Chem. Soc. 2014, 136, 945) conditions for the kinetic isomerization of a terminal alkene 6 to the Z internal alkene 7. Christoforos G. Kokotos of the University of Athens showed (J. Org. Chem. 2014, 79, 4270) that the ketone 9, used catalytically, markedly accelerated the Payne epoxidation of 8 to 10. Note that Helena M. C. Ferraz of the Universidade of São Paulo reported (Tetrahedron Lett. 2000, 41, 5021) several years ago that alkene epoxidation was also easily carried out with DMDO generated in situ from acetone and oxone. Theodore A. Betley of Harvard University prepared (Chem. Sci. 2014, 5, 1526) the allylic amine 12 by reacting the alkene 11 with 1-azidoadamantane in the presence of an iron catalyst. Rodney A. Fernandes of the Indian Institute of Technology Bombay developed (J. Org. Chem. 2014, 79, 5787) efficient conditions for the Wacker oxida­tion of a terminal alkene 6 to the methyl ketone 13. Yong-Qiang Wang of Northwest University oxidized (Org. Lett. 2014, 16, 1610) the alkene 6 to the enone 14. Peili Teo of the National University of Singapore devised (Chem. Commun. 2014, 50, 2608) conditions for the Markovnikov hydration of the alkene 6 to the alcohol 15. Internal alkenes were inert under these conditions, but Yoshikazo Kitano of the Tokyo University of Agriculture and Technology effected (Synthesis 2014, 46, 1455) the Markovnikov amination (not illustrated) of more highly substituted alkenes.

Substituted Benzenes: The Garg Synthesis of Tubingensin A

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Organic Chemistry ◽  
University Of Pennsylvania ◽  
Ni Catalyst ◽  
Indiana University ◽  
Aryl Iodide ◽  
Shanghai Institute ◽  
Peking University ◽  
Normal University ◽  
La Jolla ◽  
The University

John F. Hartwig of the University of California, Berkeley devised (Science 2014, 343, 853) conditions for the regioselective silylation of an arene 1 to give 2. The silyl group can directly be converted, inter alia, to halo, amino, alkyl, or hydroxyl. Jin-Quan Yu of Scripps La Jolla effected (Angew. Chem. Int. Ed. 2014, 53, 2683) regioselective alkenylation of the arene 3 with 4 to give 5. Wei-Liang Duan of the Shanghai Institute of Organic Chemistry described (Org. Lett. 2014, 16, 500) a related alkenyl­ation protocol. Deping Wang of Henyang Normal University developed (Eur. J. Org. Chem. 2014, 315) inexpensive conditions for the conversion of an aryl bromide 6 to the corre­sponding phenol 7. Mamoru Tobisu and Naoto Chatani of Osaka University used (J. Am. Chem. Soc. 2014, 136, 5587) a Ni catalyst to convert the lactam 8 to the aryl boro­nate 9. Patrick J. Walsh of the University of Pennsylvania found (Adv. Synth. Catal. 2014, 356, 165) conditions for the clean monoarylation of the amide 11 with 10 to give 12. In an application of the Catellani approach, Zhi- Yuan Chen of Jiangxi Normal University coupled (Chem. Eur. J. 2014, 20, 4237) the aryl iodide 13 with 14 to give the amino ester 15. Frederic Fabis of the Université de Caen-Basse-Normandie used (Chem. Eur. J. 2014, 20, 7507) Pd to catalyze the ortho halogenation (and alkoxylation) of the N-sulfonylamide 16 to give 17. Wen Wan of Shanghai University and Jian Hao of Shanghai University and the Shanghai Institute of Organic Chemistry effected (Chem. Commun. 2014, 50, 5733) ortho azidination of the aniline 18 with 19, leading to 20. Jianbo Wang of Peking University found (Angew. Chem. Int. Ed. 2014, 53, 1364) that the N-aryloxy amide 21 could be combined with the α-diazo ester 22 to give the ortho-alkenyl phenol 23. Silas P. Cook of Indiana University uncovered (Org. Lett. 2014, 16, 2026) remarkably simple conditions for the enantiospecific cyclization of 24 (65% ee) to 25 (63% ee). The development of arynes as reactive intermediates continues unabated. Xiaoming Zeng of Xi’an Jiaotong University developed (Org. Lett. 2014, 16, 314) the reagent 27 for the bis-functionalization of the aryne derived from 26.

C–H Functionalization: The Maimone Synthesis of Podophyllotoxin

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
University Of California ◽  
University Of Illinois ◽  
Methyl Group ◽  
Du Bois ◽  
Princeton University ◽  
University Of Cambridge ◽  
Rh Catalyst ◽  
Institute Of Technology ◽  
La Jolla ◽  
The University

Matthias Beller of the Universität Rostock developed (Angew. Chem. Int. Ed. 2014, 53, 6477) a Rh catalyst for the acceptorless dehydrogenation of an alkane 1 to the alkene 2. Bhisma K. Patel of the Indian Institute of Technology Guwahati effected (Org. Lett. 2014, 16, 3086) oxidation of cyclohexane 3 and 4 to form the allylic benzoate 5. Justin Du Bois of Stanford University devised (Chem. Sci. 2014, 5, 656) an organocatalyst that mediated the hydroxylation of 6 to 7. Vladimir Gevorgyan of the University of Illinois, Chicago hydrosilylated (Nature Chem. 2014, 6, 122) 8 to give an intermediate that, after Ir-catalyzed intramolecular C–H functionalization followed by oxidation, was converted to the diacetate 9. Sukbok Chang of KAIST used (J. Am. Chem. Soc. 2014, 136, 4141) the methoxime of 10 to direct selective amination of the adjacent methyl group, leading to 11. John F. Hartwig of the University of California, Berkeley effected (J. Am. Chem. Soc. 2014, 136, 2555) diastereoselective Cu-catalyzed amination of 12 with 13 to make 14. David W. C. MacMillan of Princeton University accomplished (J. Am. Chem. Soc. 2014, 136, 6858) β-alkylation of the aldehyde 15 with acrylonitrile 16 to give 17. Yunyang Wei of the Nanjing University of Science and Technology alkenylated (Chem. Sci. 2014, 5, 2379) cyclohexane 3 with the styrene 18, leading to 19. Bin Wu of the Kunming Institute of Botany described (Org. Lett. 2014, 16, 480) the Pd-mediated cyclization of 20 to 21. Similar results using Cu catalysis were reported (Angew. Chem. Int. Ed. 2014, 53, 3496, 3706) by Yoichiro Kuninobu and Motomu Kanai of the University of Tokyo and by Haibo Ge of IUPUI. Jin-Quan Yu of Scripps La Jolla constructed (J. Am. Chem. Soc. 2014, 136, 5267) the lactam 24 by γ-alkenyl­ation of the amide 22 with 23, followed by cyclization. Philippe Dauban of CNRS Gif-sur-Yvette prepared (Eur. J. Org. Chem. 2014, 66) the useful crystalline chiron 27 by asymmetric amination of the enol triflate 26 with 25. Matthew J. Gaunt of the University of Cambridge showed (J. Am. Chem. Soc. 2014, 136, 8851) that the phenylative cyclization of 28 with 29 to 30 proceeded with near-perfect retention of absolute configuration.

Preparation of Benzene Derivatives: The Barrett Syntheses of Dehydroaltenuene B and 15G256β

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Aryl Halides ◽  
University Of Michigan ◽  
One Pot ◽  
Aromatic Carboxylates ◽  
Direct Functionalization ◽  
Aryl Tosylates ◽  
La Jolla ◽  
University Of Bristol ◽  
University Of Oslo ◽  
The University

Several new methods for the direct functionalization of Ar-H have appeared. Hisao Yoshida of Nagoya University observed (Chem. Comm. 2008, 4634) that under irradiation, TiO2 in water effected meta hydroxylation of benzonitrile 1 to give the phenol 2. Anisole showed ortho selectivity, while halo and alkyl aromatics gave mixtures. Melanie S. Sanford of the University of Michigan reported (J. Am. Chem. Soc. 2008, 130, 13285) a complementary study of Pd-catalyzed ortho acetoxylation. Jin-Quan Yu of Scripps/La Jolla developed (Angew. Chem. Int. Ed. 2008, 47, 5215) a Pd-catalyzed protocol for ortho halogenation of aromatic carboxylates such as 3. A related protocol (J. Am. Chem. Soc. 2008, 130, 17676) led to ortho arylation. Trond Vidar Hansen of the University of Oslo devised (Tetrahedron Lett. 2008, 49, 4443) a one-pot procedure for the net ortho cyanation of phenols such as 5 to the salicylnitrile 6. Robin B. Bedford of the University of Bristol, Andrew J. M. Caffyn of the University of the West Indies and Sanjiv Prashar of the Universidad Rey Juan Carlos established (Chem. Comm. 2008, 990) a Rh-catalyzed protocol for ortho arylation of phenols such as 7. Laurent Désaubry of the Université Louis Pasteur observed (Tetrahedron Lett. 2008, 49, 4588) regioselective coupling of unsymmetrical difluorobenzenes such as 9 to give the ether 10. Fuk Yee Kwong of Hong Kong Polytechnic University extended (Angew. Chem. Int. Ed. 2008, 47, 6402) Pd-mediated amination to the notoriously difficult mesylates, such as 11. John F. Hartwig of the University of Illinois reported (J. Am. Chem. Soc. 2008, 130, 13848) a related method for the amination of aryl tosylates. Hong Liu of the Shanghai Institute of Materia Medica found (Organic Lett. 2008, 10, 4513) that the Fe-catalyzed amination of aryl halides such as 13 sometimes gave mixtures of regioisomers. Hideki Yorimitsu and Koichiro Oshima of Kyoto University effected (Angew. Chem. Int. Ed. 2008, 47, 5833) Ag-catalyzed Grignard cross coupling with aryl halides, converting 15 into 16. Note that silyl aromatics such as 16 are readily reduced under dissolving metal conditions to give allyl silanes.

Enantioselective Organocatalytic C-C Ring Construction

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Conjugate Addition ◽  
Catalyst System ◽  
Max Planck ◽  
Cascade Cyclizations ◽  
Silyl Enol Ether ◽  
Northwestern University ◽  
National University ◽  
University Of Oslo ◽  
Robinson Annulation ◽  
The University

Ming Yan of Sun Yat-sen University, Guangzhou, optimized (Synlett 2010, 266) the organocatalyzed addition of 2 to a cyclic enone 1, establishing the cyclopropane 3 with high diastereo- and enantiocontrol. Benjamin List of the Max-Planck-Institut Mülheim devised (Angew. Chem. Int. Ed. 2010, 49, 4136) an organocatalyst for the enantioselective methanolysis of the anhydride 4. Other ring sizes worked as well. Hisashi Yamamoto of the University of Chicago reported (Organic Lett. 2010, 12, 2476) the organocatalyzed addition of the ketone silyl enol ether 6 to the aldehyde 7, to give the syn aldol product 8 in high ee. Gang Zhao of the University of Science and Technology, Hefei, established (Angew. Chem. Int. Ed. 2010, 49, 4467) an organocatalyst for the enantioselective addition of the allene ester 10 to 9. Marcus A. Tius of the University of Hawaii uncovered (J. Am. Chem. Soc. 2010, 132, 8266) conditions for the enantioselective Nazarov cyclization of 12 to 13. Karl A. Scheidt of Northwestern University devised (Organic Lett. 2010, 12, 2830) an easily scaled protocol for the cyclization of the prochiral diketone 14 to the β-lactone 15. Thermolysis then converted 15 to the corresponding cyclopentene. Yixin Lu of the National University of Singapore showed (Organic Lett. 2010, 12, 2278) that the simple combination of commercial cinchonidine with (+)-camphorsulfonic acid gave a catalyst that effected the room-temperature conjugate addition of 16 to 1. Hiyoshizo Kotsuki of Kochi University combined (Organic Lett. 2010, 12, 1616) 1,2-diaminocyclohexane with cyclohexane-1,2-bis carboxylate to give a similarly simple catalyst system, that effected Robinson annulation of 18 to 20. Binding an organocatalyst to a polymer simplifies recovery and reuse. Tore Hansen of the University of Oslo reported (J. Org. Chem. 2010, 75 , 1620) a bottom-up approach to such polymer-bound catalysts. The bound proline worked well for the condensation of 21 with 22. The corresponding polymeric diphenyl OTMS (Jørgensen-Hayashi) catalyst was sluggish, but it effected the three-component coupling of 24, 25, and 26 in high ee. Two cascade cyclizations warrant particular mention. The racemic cyclization of 28 is expected to be facile in the presence of HCl.

Organic Functional Group Interconversion

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Reduced Form ◽  
Ni Catalyst ◽  
Max Planck ◽  
University Of Maryland ◽  
Ru Catalyst ◽  
Maryland School ◽  
National University ◽  
Rh Catalyst ◽  
Seoul National University ◽  
The University

Alois Fürstner of the Max-Planck-Institut Mülheim devised (Angew. Chem. Int. Ed. 2013, 52, 14050) a Ru catalyst for the trans- selective hydroboration of an alkyne 1 to 2. Qingbin Liu of Hebei Normal University and Chanjuan Xi of Tsinghua University coupled (Org. Lett. 2013, 15, 5174) the alkenyl zirconocene derived from 3 with an acyl azide to give the amide 4. Chulbom Lee of Seoul National University used (Angew. Chem. Int. Ed. 2013, 52, 10023) a Rh catalyst to convert a terminal alkyne 5 to the ester 6. Laura L. Anderson of the University of Illinois, Chicago devised (Org. Lett. 2013, 15, 4830) a protocol for the conversion of a ter­minal alkyne 7 to the α-amino aldehyde 9. Dewen Dong of the Changchun Institute of Applied Chemistry developed (J. Org. Chem. 2013, 78, 11956) conditions for the monohydrolysis of a bis nitrile 10 to the monoamide 11. Aiwen Lei of Wuhan University optimized (Chem. Commun. 2013, 49, 7923) a Ni catalyst for the conversion of the alkene 12 to the enamide 13. Kazushi Mashima of Osaka University optimized (Adv. Synth. Catal. 2013, 355, 3391) a boronic ester catalyst for the conversion of an amide 14 to the ester 15. Jean- François Paquin of the Université Laval prepared (Eur. J. Org. Chem. 2013, 4325) the amide 17 by coupling an amine with the activated intermediate from reaction of an acid 16 with Xtal- Fluor E. Steven Fletcher of the University of Maryland School of Pharmacy designed (Tetrahedron Lett. 2013, 54, 4624) the azodicarbonyl dimorpholide 18 as a reagent for the Mitsunobu coupling of 19 with 20. The reduced form of 18 was readily separated by extraction into water and reoxidized. Jens Deutsch of the Universität Rostock found (Chem. Eur. J. 2013, 19, 17702) simple ligands for the Ru-mediated borrowed hydro­gen conversion of an alcohol 22 to the amine 23. Ronald T. Raines of the University of Wisconsin devised (J. Am. Chem. Soc. 2013, 135, 14936) a phosphinoester for the efficient conversion in water of an azide 24 to the diazo 25.

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