scholarly journals Preface: Modern Heterocycle Synthesis and Functionalization

Synlett ◽  
2021 ◽  
Vol 32 (02) ◽  
pp. 140-141
Author(s):  
Louis-Charles Campeau ◽  
Tomislav Rovis
Keyword(s):  
Active Pharmaceutical Ingredient ◽  
Associate Professor ◽  
Columbia University ◽  
State University ◽  
Heterocycle Synthesis ◽  
Colorado State University ◽  
University Of Toronto ◽  
Process Chemistry ◽  
The University ◽  
Small Molecule Therapeutics

obtained his PhD degree in 2008 with the late Professor Keith Fagnou at the University of Ottawa in Canada as an NSERC Doctoral Fellow. He then joined Merck Research Laboratories at Merck-Frosst in Montreal in 2007, making key contributions to the discovery of Doravirine (MK-1439) for which he received a Merck Special Achievement Award. In 2010, he moved from Quebec to New Jersey, where he has served in roles of increasing responsibility with Merck ever since. L.-C. is currently Executive Director and the Head of Process Chemistry and Discovery Process Chemistry organizations, leading a team of smart creative scientists developing innovative chemistry solutions in support of all discovery, pre-clinical and clinical active pharmaceutical ingredient deliveries for the entire Merck portfolio for small-molecule therapeutics. Over his tenure at Merck, L.-C. and his team have made important contributions to >40 clinical candidates and 4 commercial products to date. Tom Rovis was born in Zagreb in former Yugoslavia but was largely raised in southern Ontario, Canada. He earned his PhD degree at the University of Toronto (Canada) in 1998 under the direction of Professor Mark Lautens. From 1998–2000, he was an NSERC Postdoctoral Fellow at Harvard University (USA) with Professor David A. Evans. In 2000, he began his independent career at Colorado State University and was promoted in 2005 to Associate Professor and in 2008 to Professor. His group’s accomplishments have been recognized by a number of awards including an Arthur C. Cope Scholar, an NSF CAREER Award, a Fellow of the American Association for the Advancement of Science and a ­Katritzky Young Investigator in Heterocyclic Chemistry. In 2016, he moved to Columbia University where he is currently the Samuel Latham Mitchill Professor of Chemistry.

Cluster Preface: Alkene Halofunctionalization

Synlett ◽  
2018 ◽  
Vol 29 (04) ◽  
pp. 399-400
Author(s):  
Jeffrey Johnston ◽  
Tomislav Rovis
Keyword(s):  
Chemical Society ◽  
Associate Professor ◽  
Harvard University ◽  
Columbia University ◽  
State University ◽  
Inorganic Pigment ◽  
Colorado State University ◽  
University Of Toronto ◽  
The Ohio State University ◽  
The University

Jeffrey N. Johnston is a 1992 graduate of Xavier University where he completed his B.S. Chemistry degree (Honors, summa cum laude). With summer research stints in medicinal, polymer, and inorganic pigment chemistry under his belt, he transitioned to synthetic organic chemistry at The Ohio State University where he worked with Leo Paquette for his graduate work (PhD 1997). He completed postdoctoral studies with ­David Evans at Harvard University (USA) and was supported by an NIH Postdoctoral Fellowship. His independent career began in 1999 at Indiana University, where he was promoted to Professor of Chemistry before moving to Vanderbilt University in 2006. He is currently a Stevenson Professor of Chemistry. The commitment of his students and postdoctoral scholars to the discovery and development of new reactions and reagents, particularly in enantioselective catalysis, have led to numerous honors, including the Cope Scholar Award, a Fellowship from the Japan Society for the Promotion of Science, a Swiss Chemical Society Lectureship, and an Eli Lilly Grantee Award. It was graduate student Mark Dobish's discovery of the chiral proton-catalyzed enantioselective iodolactonization reaction (J. Am Chem. Soc. 2012, 134, 6068) that began his group's exploits of alkene halofunctionalization reactions for the good of chemical synthesis. Tomislav Rovis was born in Zagreb in former Yugoslavia but was largely raised in southern Ontario, Canada. He earned his PhD degree at the University of Toronto (Canada) in 1998 under the direction of Professor Mark Lautens. From 1998–2000, he was an NSERC Postdoctoral Fellow at Harvard University (USA) with Professor David A. Evans. In 2000, he began his independent career at Colorado State University and was promoted in 2005 to Associate Professor and in 2008 to Professor. His group’s accomplishments have been recognized by a number of awards including an Arthur C. Cope Scholar, an NSF CAREER Award, a Fellow of the American Association for the Advancement of Science and a ­Katritzky Young Investigator in Heterocyclic Chemistry. In 2016, he moved to Columbia University where he is currently Professor of Chemistry.

Cluster Preface: Catalytic Aerobic Oxidations

Synlett ◽  
2017 ◽  
Vol 28 (13) ◽  
pp. 1546-1547 ◽  
Author(s):  
Shannon Stahl ◽  
Tomislav Rovis
Keyword(s):  
Aerobic Oxidation ◽  
Associate Professor ◽  
Columbia University ◽  
Massachusetts Institute Of Technology ◽  
Postdoctoral Fellow ◽  
Oxidation Reactions ◽  
Colorado State University ◽  
University Of Toronto ◽  
Institute Of Technology ◽  
The University

Shannon S. Stahl was an undergraduate at the University of Illinois at Urbana-Champaign, and a graduate student at Caltech (PhD, 1997), where he worked with Professor John Bercaw. He was an NSF postdoctoral fellow with Professor Stephen Lippard at Massachusetts Institute of Technology from 1997–1999. He is currently a Professor of Chemistry at the University of Wisconsin–Madison, where he began his independent career in 1999. His research group specializes in catalysis, with an emphasis on aerobic oxidation reactions and oxygen chemistry related to energy conversion. Tomislav Rovis was born in Zagreb in former Yugoslavia but was largely raised in southern Ontario, Canada. He earned his PhD degree at the University of Toronto (Canada) in 1998 under the direction of Professor Mark Lautens. From 1998–2000, he was an NSERC Postdoctoral Fellow at Harvard University (USA) with Professor David A. Evans. In 2000, he began his independent career at Colorado State University and was promoted in 2005 to Associate Professor and in 2008 to Professor. His group’s accomplishments have been recognized by a number of awards including an Arthur C. Cope Scholar, an NSF CAREER Award, a Fellow of the American Association for the Advancement of Science and a ­Katritzky Young Investigator in Heterocyclic Chemistry. In 2016, he moved to Columbia University where he is currently Professor of Chemistry.

C–O Ring Construction: The Martín and Martín Synthesis of Teurilene

2017 ◽  
Author(s):  
Tristan H. Lambert
Keyword(s):  
Phenylboronic Acid ◽  
Gold Catalysis ◽  
State University ◽  
Max Planck ◽  
Amberlyst 15 ◽  
Colorado State University ◽  
University Of Toronto ◽  
Palladium Catalyzed ◽  
University Of Bristol ◽  
The University

Benjamin List at the Max-Planck-Institute in Mülheim reported (Angew. Chem. Int. Ed. 2013, 52, 3490) that the chiral phosphoric acid TRIP catalyzed the asymmet­ric SN2-type intramolecular etherification of 1 to produce tetrahydrofuran 2 with a selectivity factor of 82. The coupling of alkenol 3 with 4 to give the α-arylated tetra­hydropyran 5 via a method that combined gold catalysis and photoredox catalysis was disclosed (J. Am. Chem. Soc. 2013, 135, 5505) by Frank Glorius at Westfälische Wilhelms-Universität Münster. Mark Lautens at the University of Toronto reported (Org. Lett. 2013, 15, 1148) the conversion of cyclohexanedione 6 and phenylboronic acid to bicyclic ether 8 using rhodium catalysis in the presence of dienyl ligand 7. Propargylic ether 9 was found (Org. Lett. 2013, 15, 2926) by John P. Wolfe at the University of Michigan to undergo conversion to furanone 10 upon treatment with dibutylboron triflate and Hünig’s base followed by oxidation with hydrogen peroxide. Tomislav Rovis at Colorado State University demonstrated (Chem. Sci. 2013, 4, 1668) that the spirocyclic compound 13 could be prepared in enantioenriched form from 11 by a photoisomerization- coupled Stetter reaction using carbene catalyst 12. Antonio C. B. Burtoloso at the University of São Paulo reported (Org. Lett. 2013, 15, 2434) the conversion of ketone 14 to lactone 15 using samarium(II) iodide and methyl acrylate. The merger of diketone 16 and pyrone 17 in the presence of Amberlyst-15 to pro­duce (−)- tenuipyrone 18 was disclosed (Org. Lett. 2013, 15, 6) by Rongbiao Tong at the Hong Kong University of Science and Technology. Joanne E. Harvey at Victoria University of Wellington in New Zealand found (Org. Lett. 2013, 15, 2430) that tricy­clic ether 20 could be generated efficiently from dihydropyran 19 and pyrone 17 via a palladium-catalyzed double allylic alkylation cascade. Two rings and four stereocenters were generated in the construction of bicyclic ether 23 from dienol 21 and acetal 22 via a Lewis acid-mediated cascade, as reported (Org. Lett. 2013, 15, 2046) by Christine L. Willis at the University of Bristol.

scholarly journals Notes on Contributors

Philosophy ◽  
2000 ◽  
Vol 75 (3) ◽  
pp. 329-329
Keyword(s):  
Associate Professor ◽  
Recent Book ◽  
Columbia University ◽  
Cambridge University ◽  
Philip Kitcher ◽  
University Of New Mexico ◽  
University Of Toronto ◽  
Oxford University ◽  
Christ Church ◽  
The University

Notes on ContributorsGilbert Ryle (1900–76)Taught at Christ Church, Oxford from 1924–45 and was Waynflete Professor of Metaphysics at Oxford University from 1945–68. His Concept of Mind (1949) is one of the classics of twentieth century philosophy.Jennifer NagelTeaches philosophy at the University of New Mexico and the University of Toronto.Philip KitcherProfessor of Philosophy at Columbia University. He has written books and articles on a variety of topics in the philosophy of science.Achille VarziAssociate Professor of Philosophy at Columbia University. His most recent works are An Essay in Universal Semantics and Parts and Places (with Roberto Casati).Neil CooperEmeritus Professor of Philosophy, University of Dundee. He is author of The Diversity of Moral Thinking. His contributions to Philosophy include ‘Two Concepts of Morality’ (January 1996) and ‘The Art of Philosophy’ (April 1991).Stephen R. L. ClarkProfessor of Philosophy, University of Liverpool. His most recent book is Biology and Christian Ethics (forthcoming, Cambridge University Press).D. GoldstickProfessor of Philosophy, University of Toronto. His earlier contributions to Philosophy include ‘The Welfare of the Dead’ (January 1988).Colin RadfordFormerly Research Professor of Philosophy, University of Kent. Now Emeritus (since 1996).Phil DoweLecturer in Philosophy at the University of Tasmania. He works on causation, time and chance. He has published a book on causation, Physical Causation (Cambridge University Press, 2000) and is currently working on a book on time travel called ‘Backwards Causation’.

NEWS AND ANNOUNCEMENTS

PEDIATRICS ◽  
1957 ◽  
Vol 19 (4) ◽  
pp. 715-717
Keyword(s):  
Pediatric Surgery ◽  
Harvard Medical School ◽  
Early Recognition ◽  
Medical Knowledge ◽  
Associate Professor ◽  
Ohio State University ◽  
State University ◽  
Emergency Procedures ◽  
The University ◽  
Annual Summer

The Ninth Annual Summer Clinics of The Children's Hospital in Denver, Colorado will be held June 24, 25, and 26, 1957. Designed for all physicians concerned with the care of children, the course will present recent advances in medical knowledge appropriate to the first few weeks of life, and will emphasize methods for the early recognition of disease, discuss emergency procedures of value, and outline successful programs of therapy. Guest faculty this year will be Dr. Stewart H. Clifford, Assistant Clinical Professor of Pediatrics, Harvard Medical School, Dr. H. William Clatworthy, Jr., Associate Professor of Pediatric Surgery, Ohio State University, and Dr. Edith L. Potter, Professor of Pathology, Department of Obstetrics and Gynecology, The University of Chicago.

Associate Professor Khabibulla Nurmukhametovich Amirov (for the 100th anniversary of his birth)

2001 ◽  
Vol 82 (3) ◽  
pp. 234-235
Author(s):  
E. S. Valishin
Keyword(s):  
Associate Professor ◽  
100Th Anniversary ◽  
Medical Faculty ◽  
Human Anatomy ◽  
State University ◽  
Financial Difficulties ◽  
Normal Human ◽  
Peasant Family ◽  
The University ◽  
The Village

Khabibulla Nurmukhametovich Amirov was born on May 18, 1901 in the village of Tat. Tashaevo of the Nurlatsky district of Tatarstan in a working peasant family. His early desire for knowledge prompted him to move to his brother in Chita as a child, where he graduated from the parish school of the 1st stage in 1916, and in 1923 from the parish school of the 2nd stage. Having shown outstanding performance, curiosity and a great thirst for knowledge over the years of study, after graduating from college, he was sent to continue his studies at the Medical Faculty of Kazan State University. From the very first days of his stay at the university, he takes up his studies with great zeal, paying great attention to a new and unfamiliar subject normal human anatomy. However, experiencing great financial difficulties, he was forced to interrupt his studies at the university. From 1924 to 1927, the young man worked as a nurse in the Zabulachno-Pletenevsky skin and venereological dispensary of the Tatnarkomzdrav, and only after the appointment of a special family scholarship, he was able to continue his studies.

Stereocontrolled C-O Ring Construction: The Fuwa/Sasaki Synthesis of Attenol A

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Gold Catalysis ◽  
Membered Ring ◽  
Allylic Alcohol ◽  
State University ◽  
Prins Cyclization ◽  
University Of Florida ◽  
University Of Pittsburgh ◽  
Colorado State University ◽  
Institute Of Technology ◽  
The University

Since five-membered ring ethers often do not show good selectivity on equilibration, single diastereomers are best formed under kinetic control. Aaron Aponick of the University of Florida demonstrated (Organic Lett. 2008, 10, 669) that under gold catalysis, the allylic alcohol 1 cyclized to 2 with remarkable diastereocontrol. Six-membered rings also formed with high cis stereocontrol. Ian Cumpstey of Stockholm University showed (Chem. Commun. 2008, 1246) that with protic acid, allylic acetates such as 3 cyclized with clean inversion at the allylic center, and concomitant debenzylation. J. Stephen Clark of the University of Glasgow found (J. Org. Chem. 2008, 73, 1040) that Rh catalyzed cyclization of 5 proceeded with high selectivity for insertion into Ha, leading to the alcohol 6. Saumen Hajra of the Indian Institute of Technology, Kharagpur took advantage (J. Org. Chem. 2008, 73, 3935) of the reactivity of the aldehyde of 7, effecting selective addition of 7 to 8, to deliver, after reduction, the lactone 9. Tomislav Rovis of Colorado State University observed (J. Org. Chem. 2008, 73, 612) that 10 could be cyclized selectively to either 11 or 12. Nadège Lubin-Germain, Jacques Uziel and Jacques Augé of the University of Cergy- Pontoise devised (Organic Lett. 2008, 10, 725) conditions for the indium-mediated coupling of glycosyl fluorides such as 13 with iodoalkynes such as 14 to give the axial C-glycoside 15. Katsukiyo Miura and Akira Hosomi of the University of Tsukuba employed (Chemistry Lett. 2008, 37, 270) Pt catalysis to effect in situ equilibration of the alkene 16 to the more stable regioisomer. Subsequent condensation with the aldehyde 17 led via Prins cyclization to the ether 18. Paul E. Floreancig of the University of Pittsburgh showed (Angew. Chem. Int. Ed. 2008, 47, 4184) that Prins cyclization could be also be initiated by oxidation of the benzyl ether 19 to the corresponding carbocation. Chan-Mo Yu of Sungkyunkwan University developed (Organic Lett. 2008, 10, 265) a stereocontrolled route to seven-membered ring ethers, by Pd-mediated stannylation of allenes such as 21, followed by condensation with an aldehyde.

Other Methods for Carbocyclic Construction: The Porco Synthesis of (-)-Hyperibone K

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Oxidative Cyclization ◽  
Florida State University ◽  
State University ◽  
Colorado State University ◽  
Intramolecular Alkylation ◽  
University Of Wisconsin ◽  
Tokyo Institute ◽  
Institute Of Technology ◽  
University Of Bristol ◽  
The University

Varinder K. Aggarwal of the University of Bristol described (Angew. Chem. Int. Ed. 2010, 49, 6673) the conversion of the Sharpless-derived epoxide 1 into the cyclopropane 2. Christopher D. Bray of Queen Mary University of London established (Chem. Commun. 2010, 46, 5867) that the related conversion of 3 to 5 proceeded with high diastereocontrol. Javier Read de Alaniz of the University of California, Santa Barbara, extended (Angew. Chem. Int. Ed. 2010, 49, 9484) the Piancatelli rearrangement of a furyl carbinol 6 to allow inclusion of an amine 7, to give 8. Issa Yavari of Tarbiat Modares University described (Synlett 2010, 2293) the dimerization of 9 with an amine to give 10. Jeremy E. Wulff of the University of Victoria condensed (J. Org. Chem. 2010, 75, 6312) the dienone 11 with the commercial butadiene sulfone 12 to give the highly substituted cyclopentane 13. Robert M. Williams of Colorado State University showed (Tetrahedron Lett. 2010, 51, 6557) that the condensation of 14 with formaldehyde delivered the cyclopentanone 15 with high diastereocontrol. D. Srinivasa Reddy of Advinus Therapeutics devised (Tetrahedron Lett. 2010, 51, 5291) conditions for the tandem conjugate addition/intramolecular alkylation conversion of 16 to 17. Marie E. Krafft of Florida State University reported (Synlett 2010, 2583) a related intramolecular alkylation protocol. Takao Ikariya of the Tokyo Institute of Technology effected (J. Am. Chem. Soc. 2010, 132, 11414) the enantioselective Ru-mediated hydrogenation of bicyclic imides such as 18. This transformation worked equally well for three-, four-, five-, six-, and seven-membered rings. Stefan France of the Georgia Institute of Technology developed (Org. Lett. 2010, 12, 5684) a catalytic protocol for the homo-Nazarov rearrangement of the doubly activated cyclopropane 20 to the cyclohexanone 21. Richard P. Hsung of the University of Wisconsin effected (Org. Lett. 2010, 12, 5768) the highly diastereoselective rearrangement of the triene 22 to the cyclohexadiene 23. Strategies for polycyclic construction are also important. Sylvain Canesi of the Université de Québec devised (Org. Lett. 2010, 12, 4368) the oxidative cyclization of 24 to 25.

Enantioselective Synthesis of Alcohols and Amines: The Fujii/Ohno Synthesis of (+)-Lysergic Acid

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Kinetic Resolution ◽  
Lysergic Acid ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivative ◽  
State University ◽  
University Of Arkansas ◽  
Keto Ester ◽  
Colorado State University ◽  
Quaternary Center ◽  
The University

Ramón Gómez Arrayás and Juan C. Carretero of the Universidad Autónoma de Madrid effected (Chem. Commun. 2011, 47, 6701) enantioselective conjugate borylation of an unsaturated sulfone 1, leading to the alcohol 2. Robert E. Gawley of the University of Arkansas found (J. Am. Chem. Soc. 2011, 133, 19680) conditions for enantioselective ketone reduction that were selective enough to distinguish between the ethyl and propyl groups of 3 to give 4. Vicente Gotor of the Universidad de Oviedo used (Angew. Chem. Int. Ed. 2011, 50, 8387) an overexpressed Baeyer-Villiger monoxygenase to prepare 6 by dynamic kinetic resolution of 5. Li Deng of Brandeis University prepared (J. Am. Chem. Soc. 2011, 133, 12458) 8 in high ee by kinetic enantioselective migration of the alkene of racemic 7. Bernhard Breit of the Freiburg Institute for Advanced Studies established (J. Am. Chem. Soc. 2011, 133, 20746) the oxygenated quaternary center of 10 by the addition of benzoic acid to the allene 9. Keith R. Fandrick of Boehringer Ingelheim constructed (J. Am. Chem. Soc. 2011, 133, 10332) the oxygenated quaternary center of 13 by enantioselective addition of the propargylic nucleophile 12 to 11. Yian Shi of Colorado State University devised (J. Am. Chem. Soc. 2011, 133, 12914) conditions for the enantioselective transamination of the α-keto ester 14 to the amine 15. Professor Deng added (Adv. Synth. Catal. 2011, 353, 3123) 18 to an enone 17 to give the protected amine 19. Song Ye of the Institute of Chemistry, Beijing effected (J. Am. Chem. Soc. 2011, 133, 15894) elimination/addition of an unsaturated acid chloride 20 to give the γ-amino acid derivative 22. Frank Glorius of the Universität Münster added (Angew. Chem. Int. Ed. 2011, 50, 1410) an aldehyde 23 to 24 to give the amide 25. Sentaro Okamoto of Kanagawa University designed (J. Org. Chem. 2011, 76, 6678) an organocatalyst for the enantioselective Steglich rearrangement of 26, creating the aminated quaternary center of 27. Most impressive of all was the report (Org. Lett. 2011, 13, 5460) by Hélène Lebel of the Université de Montréal of the direct enantioselective C–H amination of 28 to give 29.

C–O Ring Formation

2017 ◽  
Author(s):  
Tristan H. Lambert
Keyword(s):  
Science And Technology ◽  
State University ◽  
University Of Michigan ◽  
Colorado State University ◽  
Boston University ◽  
Chapel Hill ◽  
Chiral Phosphoric Acid ◽  
National University ◽  
University Of Bristol ◽  
The University

The enantioselective bromocyclization of dicarbonyl 1 to form dihydrofuran 3 using thiocarbamate catalyst 2 was developed (Angew. Chem. Int. Ed. 2013, 52, 8597) by Ying-Yeung Yeung at the National University of Singapore. Access to dihydrofuran 5 from the cyclic boronic acid 4 and salicylaldehyde via a morpholine-mediated Petasis borono-Mannich reaction was reported (Org. Lett. 2013, 15, 5944) by Xian-Jin Yang at East China University of Science and Technology and Jun Yang at the Shanghai Institute of Organic Chemistry. Chiral phosphoric acid 7 was shown (Angew. Chem. Int. Ed. 2013, 52, 13593) by Jianwei Sun at the Hong Kong University of Science and Technology to catalyze the enantioselective acetalization of diol 6 to form tetrahydrofuran 8 with high stereoselectivity. Jan Deska at the University of Cologne reported (Org. Lett. 2013, 15, 5998) the conversion of glutarate ether 9 to enantiopure tetrahy­drofuranone 10 by way of an enzymatic desymmetrization/oxonium ylide rearrange­ment sequence. Perali Ramu Sridhar at the University of Hyderabad demonstrated (Org. Lett. 2013, 15, 4474) the ring-contraction of spirocyclopropane tetrahydropyran 11 to produce tetrahydrofuran 12. Michael A. Kerr at the University of Western Ontario reported (Org. Lett. 2013, 15, 4838) that cyclopropane hemimalonate 13 underwent conver­sion to vinylbutanolide 14 in the presence of LiCl and Me₃N•HCl under microwave irradiation. Eric M. Ferreira at Colorado State University developed (J. Am. Chem. Soc. 2013, 135, 17266) the platinum-catalyzed bisheterocyclization of alkyne diol 15 to fur­nish the bisheterocycle 16. Chiral sulfur ylides such as 17, which can be synthesized easily and cheaply, were shown (J. Am. Chem. Soc. 2013, 135, 11951) by Eoghan M. McGarrigle at the University of Bristol and University College Dublin and Varinder K. Aggarwal at the University of Bristol to stereoselectively epoxidize a variety of alde­hydes, as exemplified by 18. The amine 20-catalyzed tandem heteroconjugate addition/Michael reaction of quinol 19 and cinnamaldehyde to produce bicycle 21 with very high ee was reported (Chem. Sci. 2013, 4, 2828) by Jeffrey S. Johnson at the University of North Carolina, Chapel Hill. Quinol ether 22 underwent facile photorearrangement–cycloaddition to 23 under irradiation, as reported (J. Am. Chem. Soc. 2013, 135, 17978) by John A. Porco, Jr. at Boston University and Corey R. J. Stephenson, now at the University of Michigan.

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