Literature DB >> 28229149

Recent advances in organocatalytic enantioselective transfer hydrogenation.

Ana Maria Faísca Phillips1, Armando J L Pombeiro.   

Abstract

The organocatalytic reduction of C[double bond, length as m-dash]C and C[double bond, length as m-dash]N double bonds with biomimetic reductants, e.g. Hantzsch 1,4-dihydropyridine esters and benzothiazolines, is reviewed. Very high yields and stereoselectivities have been achieved with a variety of catalysts, including chiral amines, thioureas and phosphoric acids, even with loadings equivalent to those of transition metal-catalyzed reactions in some cases. Reductive amination reactions and the dearomatization of heteroaromatic substrates are the subject of more than one half of the contributions. Of lately, methodologies based on kinetic resolution, cascade reactions involving transfer hydrogenation and the development of novel reductants have become prominent in an area which brings great prospects for the future of target oriented-synthesis.

Entities:  

Year:  2017        PMID: 28229149     DOI: 10.1039/c7ob00113d

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  7 in total

1.  CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes.

Authors:  Yujing Zhou; Jeffrey S Bandar; Richard Y Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

2.  Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes.

Authors:  Yuk-Cheung Chan; Marcus H Sak; Scott A Frank; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-07       Impact factor: 15.336

3.  Silica gel-immobilized multidisciplinary materials applicable in stereoselective organocatalysis and HPLC separation.

Authors:  J Tůma; M Kohout
Journal:  RSC Adv       Date:  2018-01-03       Impact factor: 4.036

4.  Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones.

Authors:  Christopher R Shugrue; Aaron L Featherston; Rachel M Lackner; Angela Lin; Scott J Miller
Journal:  J Org Chem       Date:  2018-04-05       Impact factor: 4.354

5.  Ternary complexes of chiral disulfonimides in transfer-hydrogenation of imines: the relevance of late intermediates in ion pair catalysis.

Authors:  Matej Žabka; Ruth M Gschwind
Journal:  Chem Sci       Date:  2021-11-17       Impact factor: 9.825

6.  Mechanistic insight into the catalytic hydrogenation of nonactivated aldehydes with a Hantzsch ester in the presence of a series of organoboranes: NMR and DFT studies.

Authors:  Go Hamasaka; Hiroaki Tsuji; Masahiro Ehara; Yasuhiro Uozumi
Journal:  RSC Adv       Date:  2019-04-02       Impact factor: 3.361

7.  Design and synthesis of chiral and regenerable [2.2]paracyclophane-based NAD(P)H models and application in biomimetic reduction of flavonoids.

Authors:  Zhou-Hao Zhu; Yi-Xuan Ding; Bo Wu; Yong-Gui Zhou
Journal:  Chem Sci       Date:  2020-09-10       Impact factor: 9.825

  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.