SYNTHESIS OF CYCLIC AMINES AND ALLYLIC SULFIDES BY PHENYLTHIO MIGRATION OF BETA-HYDROXY SULFIDES

Authors
COLDHAM I WARREN S
Citation
I. Coldham et S. Warren, SYNTHESIS OF CYCLIC AMINES AND ALLYLIC SULFIDES BY PHENYLTHIO MIGRATION OF BETA-HYDROXY SULFIDES, Journal of the Chemical Society. Perkin transactions. I, (14), 1993, pp. 1637-1656
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
14
Year of publication
1993
Pages
1637 - 1656
Database
ISI
SICI code
0300-922X(1993):14<1637:SOCAAA>2.0.ZU;2-G
Abstract
Rearrangement of beta-hydroxy sulfides proceeds stereospecifically wit h capture of the episulfonium ion by the nitrogen atom of an amide. Al most quantitative yields of substituted pyrrolidines are obtained usin g a sulfonamide as the intramolecular nucleophile and with activation by trimethylsilyl trifluoromethanesulfonate (TMSOTf). With a free amin e no cyclization takes place, but instead allylic sulfides are formed.