Literature DB >> 23754605

A palladium-catalyzed enantioselective addition of arylboronic acids to cyclic ketimines.

Guoqiang Yang1, Wanbin Zhang.   

Abstract

Sly as Nicox: A palladium-catalyzed addition of arylboronic acids to ketimines has been developed to efficiently provide products in up to 99 % yield and 96 % ee. The reactions could be run under aerobic conditions and with unpurified trifluoroethanol (TFE). A pyrrolidine compound bearing a chiral α-tertiary amine was synthesized in several steps without loss of enantioselectivity. TFA = trifluoroacetate.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amines; asymmetric catalysis; enantioselectivity; heterocycles; palladium

Year:  2013        PMID： 23754605     DOI： 10.1002/anie.201302861

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

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Authors:  Chibueze I Onyeagusi; Steven J Malcolmson
Journal:  ACS Catal       Date:  2020-10-12       Impact factor: 13.084

2.  Catalytic enantioselective addition of Grignard reagents to aromatic silyl ketimines.

Authors:  Jiawei Rong; Juan F Collados; Pablo Ortiz; Ravindra P Jumde; Edwin Otten; Syuzanna R Harutyunyan
Journal:  Nat Commun       Date:  2016-12-23       Impact factor: 14.919

3.  Ni(II)-catalyzed asymmetric alkenylations of ketimines.

Authors:  Mao Quan; Xiaoxiao Wang; Liang Wu; Ilya D Gridnev; Guoqiang Yang; Wanbin Zhang
Journal:  Nat Commun       Date:  2018-06-08       Impact factor: 14.919

4.  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

5.  Enantioselective synthesis of α-amino ketones through palladium-catalyzed asymmetric arylation of α-keto imines.

Authors:  Wei Wen; Zhao-Pin Ai; Chang-Lin Yang; Chao-Xing Li; Zhu-Lian Wu; Tian Cai; Qi-Xiang Guo
Journal:  Chem Sci       Date:  2022-03-07       Impact factor: 9.825

6.  Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines.

Authors:  Charlotte A Osborne; Thomas B D Endean; Elizabeth R Jarvo
Journal:  Org Lett       Date:  2015-10-27       Impact factor: 6.005

7.  Cu-catalyzed asymmetric addition of alcohols to β,γ-alkynyl-α-imino esters for the construction of linear chiral N,O-ketals.

Authors:  Cheng Sheng; Zheng Ling; Yicong Luo; Wanbin Zhang
Journal:  Nat Commun       Date:  2022-01-20       Impact factor: 14.919
  7 in total

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