A study of the alkylation and rearrangement products of chiral 1,3-oxazolidine- and thiazolidine-2-thiones

Robiette, Raphaël;Dekoker-Malengreau, A;Marchand-Brynaert, Jacqueline
(2003) Heterocycles — Vol. 60, n° 3, p. 523-+ (2003)

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  • Robiette, Raphaëlorcid-logoUCLouvain
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  • Dekoker-Malengreau, A
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  • Marchand-Brynaert, JacquelineUCLouvain
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Abstract
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.
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Robiette, R., Dekoker-Malengreau, A., & Marchand-Brynaert, J. (2003). A study of the alkylation and rearrangement products of chiral 1,3-oxazolidine- and thiazolidine-2-thiones. Heterocycles, 60(3), 523-+. https://doi.org/10.3987/COM-02-9653 (Original work published 2003)