LETTER	Synlett 2006: 3100-3104   DOI: 10.1055/s-2006-949624
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Functionalized Δ3-Pyrrolines via a Ag(I)-Catalyzed Cyclization of Amino Acid Derived Allenes
Branko Mitasev, Kay M. Brummond*
Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA Fax: +1(412)6248611; e-Mail: kbrummon@pitt.edu;
Received 19 April 2006

Abstract

Diversity-oriented synthesis (DOS) of a collection of novel, highly functionalized Δ³-pyrrolines has been accomplished by a AgNO₃-catalyzed cyclization reaction of allenic amino acids that proceeds with transfer of chiral information. A new mode of cyclization of allenic benzoyl-protected amines in the Ag(I)-catalyzed reaction leading to oxazines was observed.

Key words

pyrrolines - allene - cyclization - silver catalysis - amino acid - oxazine