Gold(i)-catalyzed enantioselective synthesis of polycyclic indoline skeletons and enantiomerically enriched β-substituted tryptamine-allenes by kinetic resolution

2019 ◽  
Vol 55 (29) ◽  
pp. 4210-4213 ◽  
Author(s):  
Yan-Yan Zhang ◽  
Yin Wei ◽  
Min Shi

We have developed a gold(i)-catalyzed highly efficient kinetic resolution of indole–allene derivatives, providing polycyclic indoline skeletons in good yields with high regio- and diastereoselectivities and enantioselectivities.

Molecules ◽  
2021 ◽  
Vol 26 (24) ◽  
pp. 7475
Author(s):  
Yipeng You ◽  
Ming Yu Jin ◽  
Guanyu Tao ◽  
Xiangyou Xing

No matter through asymmetric reduction of ketones or kinetic resolution of secondary alcohols, enantioselective synthesis of the corresponding secondary alcohols is challenging when the two groups attached to the prochiral or chiral centers are spatially or electronically similar. For examples, dialkyl (sp3 vs. sp3), diaryl (sp2 vs. sp2), and aryl-alkenyl (sp2 vs. sp2) alcohols are difficult to produce with high enantioselectivities. By exploiting our recently developed Ru-catalysts of minimal stereogenicity, we reported herein a highly efficient kinetic resolution of aryl-alkenyl alcohols through hydrogen transfer. This method enabled such versatile chiral building blocks for organic synthesis as allylic alcohols, to be readily accessed with excellent enantiomeric excesses at practically useful conversions.


Author(s):  
Ruixia Liu ◽  
Jingkuo Han ◽  
Bin Li ◽  
Xian Liu ◽  
Zhao Wei ◽  
...  

A highly efficient intramolecular asymmetric reductive amination transformation catalyzed by an iridium complex of tBu-ax-Josiphos has been realized, providing an efficient access to various THIQ alkaloids.


2017 ◽  
Vol 129 (9) ◽  
pp. 2494-2498 ◽  
Author(s):  
Sri Krishna Nimmagadda ◽  
Sharath Chandra Mallojjala ◽  
Lukasz Woztas ◽  
Steven E. Wheeler ◽  
Jon C. Antilla

Author(s):  
Douglass F. Taber

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.


Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 648
Author(s):  
Yu-Hao Zhou ◽  
Yu-Zu Zhang ◽  
Zhu-Lian Wu ◽  
Tian Cai ◽  
Wei Wen ◽  
...  

A highly efficient quinine-derived primary-amine-catalyzed asymmetric aldol addition of hydroxyacetone to arylglyoxals is described. Structurally diverse anti-2,3-dihydroxy-1,4-diones were generated in high yields, with good diastereoselectivities and enantioselectivities.


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