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Paper | Special issue | Vol 54, No. 2, 2001, pp.691-704
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)47
Synthesis of 1,3-Thiazolidines from Aromatic Thioketones and N-Benzylidene α-Amino Acid Esters via 1,3-Dipolar Cycloaddition of Azomethine Ylides

Andreas Gebert, Anthony Linden, and Heinz Heimgartner*

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


The reaction of N-benzylidenephenylglycine methyl ester (2a) and N-benzylidenalanine methyl ester (2b) with thiobenzophenone (5a) and fluorene-9-thione (5b) in acetonitrile in the presence of lithium bromide and DBU gave a mixture of two corresponding diastereoisomeric [2+3] cycloadducts of types (6) and (7). The products were formed regioselectively and in good yields from the in situ generated metallo-azomethine ylides (8). The relative configurations of the two products (6c) and (7c) formed from fluorene-9-thione (5b) and 2a were established by X-Ray crystallography.