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Paper | Special issue | Vol 56, No. 1-2, 2002, pp.393-402
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)57
Stereoselective 1,3-Dipolar Cycloaddition of an Azomethine Ylide with a Chiral 1,3-Thiazole-5(4H)-thione

Andreas Gebert, Anthony Linden, Grzegorz Mloston, and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland


The reaction of cis-1-methyl-2,3-diphenylaziridine (2) with racemic 4-benzyl-4-methyl-2-phenyl-1,3-thiazole-5(4H)-thione (rac-1b) in toluene at 100-105°C gave a single spirocyclic [2+3] cycloadduct (rac-5). Its structure and relative configuration was established by X-Ray crystallography. Starting with enantiomerically pure (R)-1b and (S)-1b, the enantiomers (4R,5R,7S,9R)-5 and (4S,5S,7R,9S)-5, respectively, were formed in a regio- and stereoselective 1,3-dipolar cycloaddition of the in situ generated (E,Z)-configured N-methyl-1,3-diphenylazomethine ylide (4).