Literature DB >> 15646949

Highly enantioselective amination of alpha-substituted alpha-cyanoacetates with chiral catalysts accessible from both quinine and quinidine.

Xiaofeng Liu1, Hongming Li, Li Deng.   

Abstract

[Reaction: see text] The catalytic construction of nitrogen-substituted quaternary stereocenters is an important and challenging task in asymmetric synthesis. In this paper, we describe the use of 6'-OH-modified cinchona alkaloids that are accessible from either quinine or quinidine for the development of a highly enantioselective amination of alpha,alpha-disubstituted carbonyl compounds that is suitable for the creation of nitrogen-substituted quaternary stereocenters in either the R or S configuration.

Entities:  

Year:  2005        PMID: 15646949     DOI: 10.1021/ol048190w

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids.

Authors:  Hongming Li; Baomin Wang; Li Deng
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

2.  Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.

Authors:  Hideyuki Konishi; Tin Yiu Lam; Jeremiah P Malerich; Viresh H Rawal
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

3.  Catalytic Enantioselective Electrophilic Aminations of Acyclic α-Alkyl β-Carbonyl Nucleophilies.

Authors:  Xiaofeng Liu; Bingfeng Sun; Li Deng
Journal:  Synlett       Date:  2009-06       Impact factor: 2.454

4.  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

Review 5.  Organocatalyzed asymmetric alpha-oxidation, alpha-aminoxylation and alpha-amination of carbonyl compounds.

Authors:  Tirayut Vilaivan; Worawan Bhanthumnavin
Journal:  Molecules       Date:  2010-02-11       Impact factor: 4.411

6.  Readily Available Chiral Benzimidazoles-Derived Guanidines as Organocatalysts in the Asymmetric α-Amination of 1,3-Dicarbonyl Compounds.

Authors:  Llorenç Benavent; Francesco Puccetti; Alejandro Baeza; Melania Gómez-Martínez
Journal:  Molecules       Date:  2017-08-11       Impact factor: 4.411

7.  Mechanochemistry assisted asymmetric organocatalysis: A sustainable approach.

Authors:  Pankaj Chauhan; Swapandeep Singh Chimni
Journal:  Beilstein J Org Chem       Date:  2012-12-06       Impact factor: 2.883

8.  Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters.

Authors:  B M Trost; J S Tracy; T Saget
Journal:  Chem Sci       Date:  2018-02-14       Impact factor: 9.825

  8 in total

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