Synthesis 2014; 46(10): 1348-1354
DOI: 10.1055/s-0033-1341051
special topic
© Georg Thieme Verlag Stuttgart · New York

Rh2(OAc)4 and Chiral Phosphoric Acid Cocatalyzed Highly Diastereo- and Enantioselective Four-Component Reactions: Facile Synthesis of Chiral α,β-Diamino Acid Derivatives

Changcheng Jing
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, and Department of Chemistry, East China Normal University, Shanghai, 200062, P. R. of China   Fax: +86(21)62221235   Email: whu@chem.ecnu.edu.cn
,
Dong Xing
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, and Department of Chemistry, East China Normal University, Shanghai, 200062, P. R. of China   Fax: +86(21)62221235   Email: whu@chem.ecnu.edu.cn
,
Yu Qian
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, and Department of Chemistry, East China Normal University, Shanghai, 200062, P. R. of China   Fax: +86(21)62221235   Email: whu@chem.ecnu.edu.cn
,
Wenhao Hu*
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, and Department of Chemistry, East China Normal University, Shanghai, 200062, P. R. of China   Fax: +86(21)62221235   Email: whu@chem.ecnu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 02 February 2014

Accepted: 25 February 2014

Publication Date:
27 March 2014 (online)

Abstract

A highly diastereo- and enantioselective four-component reaction of a diazo ketone with two molecules of anilines and ethyl glyoxylate was achieved under Rh2(OAc)4 and chiral phosphoric acid cocatalyzed conditions. This transformation proceeds through a Mannich-type trapping of the ammonium ylide generated from metal carbene and one molecule of aniline with iminoester derived from another molecule of aniline and ethyl glyoxylate. With this method, a series of chiral α,β-diamino acid derivatives were efficiently constructed in good yields and with good to excellent diastereo- and enantioselectivities.

Supporting Information

 
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