2-Oxiranyl and 2-aziridinyl thiazoles 3 and 7 have been prepared by lithiation of thiazoles la and Ib and reaction with alpha-halogenocarbonyl compounds [1a, 1c-d] and alpha-halogenoimines [1b], respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
Lithiation of Cinnamyl Chloride: Stereoselective Synthesis of Propargylic Oxiranes and Aziridines
Propargylic oxiranes 4a-e and aziridines 8a-c have been prepared from cinnamyl chloride through lithiation-alkylation with alpha -halo carbonyl compounds and alpha -chloro imines, respectively. The reaction with substituted alpha -halo carbonyl compounds and alpha -chloro imines proved to be highly E diastereoselective.