Literature DB >> 19569686

Enantioselective hydrogenation of N-H imines.

Guohua Hou1, Francis Gosselin, Wei Li, J Christopher McWilliams, Yongkui Sun, Mark Weisel, Paul D O'Shea, Cheng-yi Chen, Ian W Davies, Xumu Zhang.   

Abstract

N-H ketoimines 3a-3v are readily prepared in high yield via organometallic addition to nitriles and isolated as corresponding bench-stable hydrochloride salts. Homogeneous asymmetric hydrogenation of unprotected N-H ketoimines 3a-3v using Ir-(S,S)-f-binaphane as catalyst provides chiral amines 4a-4v in 90-95% yield with enantioselectivities up to 95% ee.

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Year:  2009        PMID： 19569686     DOI： 10.1021/ja903319r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  10 in total

1.  Delayed catalyst function enables direct enantioselective conversion of nitriles to NH2-amines.

Authors:  Shaochen Zhang; Juan Del Pozo; Filippo Romiti; Yucheng Mu; Sebastian Torker; Amir H Hoveyda
Journal:  Science       Date:  2019-04-05       Impact factor: 47.728

2.  Screening and characterization of a diverse panel of metagenomic imine reductases for biocatalytic reductive amination.

Authors:  James R Marshall; Peiyuan Yao; Sarah L Montgomery; James D Finnigan; Thomas W Thorpe; Ryan B Palmer; Juan Mangas-Sanchez; Richard A M Duncan; Rachel S Heath; Kirsty M Graham; Darren J Cook; Simon J Charnock; Nicholas J Turner
Journal:  Nat Chem       Date:  2020-12-30       Impact factor: 24.427

3.  Design and synthesis of 3,3'-triazolyl biisoquinoline N,N'-dioxides via Hiyama cross-coupling of 4-trimethylsilyl-1,2,3-triazoles.

Authors:  Shiyu Sun; Carlyn Reep; Chenrui Zhang; Burjor Captain; Roberto Peverati; Norito Takenaka
Journal:  Tetrahedron Lett       Date:  2021-08-21       Impact factor: 2.032

4.  Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea.

Authors:  Qingyang Zhao; Jialin Wen; Renchang Tan; Kexuan Huang; Pedro Metola; Rui Wang; Eric V Anslyn; Xumu Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-18       Impact factor: 15.336

5.  A facile circular dichroism protocol for rapid determination of enantiomeric excess and concentration of chiral primary amines.

Authors:  Sonia Nieto; Justin M Dragna; Eric V Anslyn
Journal:  Chemistry       Date:  2010-01-04       Impact factor: 5.236

6.  Catalytic diastereo- and enantioselective additions of versatile allyl groups to N-H ketimines.

Authors:  Hwanjong Jang; Filippo Romiti; Sebastian Torker; Amir H Hoveyda
Journal:  Nat Chem       Date:  2017-07-17       Impact factor: 24.427

7.  Raising the pKa limit of "soft" nucleophiles in palladium-catalyzed allylic substitutions: application of diarylmethane pronucleophiles.

Authors:  Sheng-Chun Sha; Jiadi Zhang; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2013-11-12       Impact factor: 15.419

8.  In situ generation of N-unsubstituted imines from alkyl azides and their applications for imine transfer via copper catalysis.

Authors:  Lu Hu; Yahu A Liu; Xuebin Liao
Journal:  Sci Adv       Date:  2017-08-09       Impact factor: 14.136

9.  Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines.

Authors:  Jianzhong Chen; Zhenfeng Zhang; Bowen Li; Feilong Li; Yulin Wang; Min Zhao; Ilya D Gridnev; Tsuneo Imamoto; Wanbin Zhang
Journal:  Nat Commun       Date:  2018-11-27       Impact factor: 14.919

10.  Primary trifluoroborate-iminiums enable facile access to chiral α-aminoboronic acids via Ru-catalyzed asymmetric hydrogenation and simple hydrolysis of the trifluoroborate moiety.

Authors:  Andrej Šterman; Izidor Sosič; Zdenko Časar
Journal:  Chem Sci       Date:  2022-01-26       Impact factor: 9.825
  10 in total

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