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

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 acid

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