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Synlett 2001; 2001(Special Issue): 0914-0919
DOI: 10.1055/s-2001-14665
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Mild Pd(OAc)2/PPh3 Catalyzed Cyclization Reactions of 2-Vinylazetidines with Heterocumulenes: An Atom-Economy Synthesis of Tetrahydropyrimidinone, Tetrahydropyrimidinimine, and Thiazinanimine Analogs

Gyro A. Inman* , David C. D. Butler, H. Alper
  • *Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5; E-mail: halper@science.uottawa.ca
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Publication Date:
31 December 2001 (online)

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A versatile method for the reaction of N-alkyl-2-vinylazetidines with heterocumulenes has been established using a Pd(OAc)2/PPh3 catalyst system at room temperature. Minor modifications in the design of either substrate allowed for the optimization of product yield. Evidence for π-allylpalladium formation was obtained from the reaction of trans-1-butyl-4-methyl-2-vinylazetidine, which afforded a cis/trans mixture of products arising from stereochemical inversion through η 3-η 1-η 3 isomerization.

tetrahydropyrimidin-2-ones - tetrahydropyrimidin-2-ylidenes - [1,3]thiazinan-2-ylidenes - pi-allylpalladium complexes