Literature DB >> 15839665

Dynamic kinetic resolution catalyzed by Ir axially chiral phosphine catalyst: asymmetric synthesis of anti aromatic beta-hydroxy-alpha-amino acid esters.

Kazuishi Makino1, Yasuhiro Hiroki, Yasumasa Hamada.   

Abstract

The anti selective hydrogenation of alpha-amino-beta-keto esters via dynamic kinetic resolution was achieved for the first time by using the iridium-MeOBIPHEP catalyst in asymmetric synthesis of anti aromatic beta-hydroxy-alpha-amino acid esters with excellent diastereo- and enantioslectivities. Acetic acid as a solvent and sodium acetate as an additive affected dramatically the yield and the enantioselectivity, respectively. The product anti aromatic beta-hydroxy-alpha-amino acid esters are useful for synthesis of pharmaceuticals and natural products.

Entities:  

Year:  2005        PMID: 15839665     DOI: 10.1021/ja0432113

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


  6 in total

1.  Enantio- and diastereoselective synthesis of (R,R)-beta-methoxytyrosine.

Authors:  David C Cranfill; Mark A Lipton
Journal:  Org Lett       Date:  2007-08-03       Impact factor: 6.005

2.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

3.  Stereocontrolled synthesis of syn-β-Hydroxy-α-amino acids by direct aldolization of pseudoephenamine glycinamide.

Authors:  Ian B Seiple; Jaron A M Mercer; Robin J Sussman; Ziyang Zhang; Andrew G Myers
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-01       Impact factor: 15.336

4.  Catalytic Asymmetric Direct Aldol Reaction of α-Alkyl Azlactones and Aliphatic Aldehydes.

Authors:  Yang Zheng; Li Deng
Journal:  Chem Sci       Date:  2015-08-04       Impact factor: 9.825

5.  Enantioselective synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters: application to the total synthesis of (+)-alexine.

Authors:  Lu Yu; Peter Somfai
Journal:  RSC Adv       Date:  2019-01-21       Impact factor: 4.036

6.  A versatile catalyst system for enantioselective synthesis of 2-substituted 1,4-benzodioxanes.

Authors:  Eugene Chong; Bo Qu; Yongda Zhang; Zachary P Cannone; Joyce C Leung; Sergei Tcyrulnikov; Khoa D Nguyen; Nizar Haddad; Soumik Biswas; Xiaowen Hou; Katarzyna Kaczanowska; Michał Chwalba; Andrzej Tracz; Stefan Czarnocki; Jinhua J Song; Marisa C Kozlowski; Chris H Senanayake
Journal:  Chem Sci       Date:  2019-03-13       Impact factor: 9.825

  6 in total

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