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Synthesis 2014; 46(10): 1348-1354
DOI: 10.1055/s-0033-1341051
DOI: 10.1055/s-0033-1341051
special topic
Rh2(OAc)4 and Chiral Phosphoric Acid Cocatalyzed Highly Diastereo- and Enantioselective Four-Component Reactions: Facile Synthesis of Chiral α,β-Diamino Acid Derivatives
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.
Key words
four-component reaction - metal carbene - chiral Brønsted acid - ammonium ylide - chiral α,β-diamino acidSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
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