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Communication | Special issue | Vol 62, No. 1, 2004, pp.217-222
Published online, 18th November, 2003
DOI: 10.3987/COM-03-S(P)56
A Uniquely Accessible Route to the Diastereoselective Synthesis of Azetine Derivatives

Narendra B. Ambhaikar, Marike Herold, and Dennis C. Liotta*

*Department of Chemistry, Emory University, 1521 Pierce Drive Atlanta, Georgia 30322, U.S.A.

Abstract

In the diastereoselective additions of chlorotitanium enolate of N-propionylthiazolidine-2-thione (2) to nitriles via the corresponding N-metalloaldimines (Al, B, Zr as metals), thiazolidine-2-thioneazetines (3) are preferentially formed over the dihydropyrimidinones (4), with the ratios of compounds (3/4) ranging from 5:1 to 17:1 (for R = phenyl, 1-naphthyl and 2-thienyl).