Tetrahedron Letters p. 2311 - 2314 (1996)
Update date:2022-09-26
Topics: Stereoselective synthesis nucleophilic epoxidation β-amino-α-hydroxy acid derivatives 1-arylthio-1-nitroalkenes
Ambroise, Lydia
Jackson, Richard F.W.
Reaction of lithium t-butylperoxide with 1-arylthio-1-nitroalkenes 5, prepared by condensation of (4-tolylthio)nitromethane with N-(Boc)-protected α-amino aldehydes, leads to the formation of oxazolidinones rather than the expected oxitranes. Initially, a mixture of cis 8 and trans 9 diastereoisomers is formed, but upon exposure to silica gel complete conversion to the cis-diastereoisomers 8 takes place.
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