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Paper | Regular issue | Vol 60, No. 3, 2003, pp.523-536
Published online, 31st January, 2003
DOI: 10.3987/COM-02-9653
A Study of the Alkylation and Rearrangement Products of Chiral 1,3-Oxazolidine- and Thiazolidine-2-thiones

Raphaël Robiette, Anny Dekoker-Malengreau, and Jacqueline Marchand-Brynaert*

*Department of Organic and Medical Chemistry, Catholic University of Louvain, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium


Homochiral 1,3-oxazolidine-2-thiones and 1,3-thiazolidine-2-thiones are useful chiral auxiliaries in asymmetric synthesis. Our interest in chiral amino dienes drove us to consider the preparation of dienes (1a) and (1b) bearing those auxiliaries. Trying to synthesize such dienes by alkylation of the corresponding heterocycles with 1,4-dihalogeno-2-butenes, we found several rearrangement reactions leading to new compounds that we fully characterized. In particular, we found a new access towards 4-vinyl-1,3-thiazolidin-2-ones.