Literature DB >> 11982347

Highly effective chiral ortho-substituted BINAPO ligands (o-BINAPO): applications in Ru-catalyzed asymmetric hydrogenations of beta-aryl-substituted beta-(acylamino)acrylates and beta-keto esters.

Yong-Gui Zhou1, Wenjun Tang, Wen-Bo Wang, Wenge Li, Xumu Zhang.   

Abstract

A novel family of chiral ortho-substituted BINAPO ligands (o-BINAPO) were synthesized from BINOL, and their Ru complexes were highly efficient catalysts for asymmetric hydrogenation of beta-aryl-substituted beta-(acylamino)acrylates and beta-aryl-substituted beta-keto esters. The Ru-bisphosphinite catalysts can tolerate an E/Z mixture of beta-aryl-substituted beta-(acylamino)acrylates. These highly enantioselective hydrogenations provide a useful way to prepare beta-aryl-substituted beta-amino acids and beta-hydroxyl acids.

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Year:  2002        PMID： 11982347     DOI： 10.1021/ja020121u

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


  8 in total

1.  Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry.

Authors:  Sheng Guo; Jiaqi Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-11       Impact factor: 15.336

2.  Practical and highly enantioselective synthesis of beta-alkynyl-beta-amino esters through Ag-catalyzed asymmetric mannich reactions of silylketene acetals and alkynyl imines.

Authors:  Nathan S Josephsohn; Emma L Carswell; Marc L Snapper; Amir H Hoveyda
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

3.  The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: enantioselective synthesis of beta-amino acids.

Authors:  Jun Song; Yi Wang; Li Deng
Journal:  J Am Chem Soc       Date:  2006-05-10       Impact factor: 15.419

4.  Enantioselective hydrogenation of alpha-aminomethylacrylates containing a free NH group for the synthesis of beta-amino acid derivatives.

Authors:  Liqin Qiu; Mahavir Prashad; Bin Hu; Kapa Prasad; Oljan Repic; Thomas J Blacklock; Fuk Yee Kwong; Stanton H L Kok; Hang Wai Lee; Albert S C Chan
Journal:  Proc Natl Acad Sci U S A       Date:  2007-10-17       Impact factor: 11.205

5.  Copper-catalyzed asymmetric conjugate reduction as a route to novel beta-azaheterocyclic acid derivatives.

Authors:  Matthew P Rainka; Yimon Aye; Stephen L Buchwald
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

6.  Remarkably diastereoselective synthesis of a chiral biphenyl diphosphine ligand and its application in asymmetric hydrogenation.

Authors:  Liqin Qiu; Jing Wu; Shusun Chan; Terry T-L Au-Yeung; Jian-Xin Ji; Rongwei Guo; Cheng-Chao Pai; Zhongyuan Zhou; Xingshu Li; Qing-Hua Fan; Albert S C Chan
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

7.  Combined Theoretical and Experimental Studies Unravel Multiple Pathways to Convergent Asymmetric Hydrogenation of Enamides.

Authors:  Jianping Yang; Luca Massaro; Suppachai Krajangsri; Thishana Singh; Hao Su; Emanuele Silvi; Sudipta Ponra; Lars Eriksson; Mårten S G Ahlquist; Pher G Andersson
Journal:  J Am Chem Soc       Date:  2021-12-14       Impact factor: 15.419

8.  Synthesis of N-aryl β-amino acid derivatives via Cu(ii)-catalyzed asymmetric 1,4-reduction in air.

Authors:  Min Li; Hong-Feng Xia; Li-Yao Yang; Tao Hong; Lin-Jie Xie; Shijun Li; Jing Wu
Journal:  RSC Adv       Date:  2019-03-20       Impact factor: 4.036
  8 in total

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