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Organic letters

Lewis acid promoted highly diastereoselective Petasis Borono-Mannich reaction: efficient synthesis of optically active β,γ-unsaturated α-amino acids.


PMID 22480132

Abstract

An efficient and straightforward method for the preparation of highly enantiomerically enriched β,γ-unsaturated α-amino acid derivatives by a Lewis acid promoted diastereoselective Petasis reaction of vinylboronic acid, N-tert-butanesulfinamide, and glyoxylic acid has been developed. The synthetic utilities of the approach were demonstrated by the rapid and convenient construction of challenging cyclopenta[c]proline derivatives.

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