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Efficient Synthesis of β²-Amino Acid by Homologation of α-Amino Acids Involving the Reformatsky Reaction and Mannich-Type Imminium Electrophile

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Roba Moumne,^†^‡ Solange Lavielle,^† and Philippe Karoyan*^†

Synthses, Structures et Fonctions des Molcules Bioactives, CNRS/UMR 7613, Universit Pierre et Marie Curie, 4, Place Jussieu, 75252, Paris Cedex 05, France, and Senn Chemicals AG Industriestrasse, 12 P.O. Box 267, CH-8157 Dielsdorf, Switzerland karoyan@ccr.jussieu.fr

J. Org. Chem., 2006, 71 (8), pp 3332–3334

DOI: 10.1021/jo060316a

Publication Date (Web): March 21, 2006

†

Université Pierre et Marie Curie.

‡

Senn Chemicals AG Industriestrasse.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Development of new methods for the synthesis of β-amino acids is important as polymers of these compounds are promising peptidomimetic candidates in medicinal chemistry. We report here our findings on a new and highly efficient general strategy for the synthesis of β²-amino acids by homologation of α-amino acids, involving the Reformatsky reaction and Mannich-type imminium electrophile.

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Published In Issue April 14, 2006
Received February 15, 2006

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Efficient Synthesis of β²-Amino Acid by Homologation of α-Amino Acids Involving the Reformatsky Reaction and Mannich-Type Imminium Electrophile