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, Email: kbrummonpitt.edu

B. Mitasev, K. M. Brummond, Synlett, 2006, 3100-3104.

DOI: 10.1055/s-2006-949624

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Abstract

Synthesis of various 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 also observed.

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Key Words

pyrrolines, allenes, cyclization, silver catalysis, amino acid, oxazines

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ID: J60-Y2006-4760