a study of the alkylation and rearrangement products of chiral 1,3-oxazolidine- and Thiazolidine-2-thiones

摘要

Homochiral 1,3-oxazolidine-thiones and 1,3-thiazolidine-2-thiones are useful chiral auxiliaries in asymmetric synthesis. Our interest in chiral amino dienes drove us to consider th 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 chracterized. In particular, we found a new access towards 4-vinyl-1,3-thiazolidin-2-ones.