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Reactions with aziridines, 46. Ring opening of stilbene imines by thiophenolate
Author(s) -
Mall Thomas,
Stamm Helmut
Publication year - 1988
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19881210722
Subject(s) - chemistry , diastereomer , aziridine , protonation , ring (chemistry) , stereochemistry , bicyclic molecule , medicinal chemistry , organic chemistry , ion
Ring opening by thiophenolate of cis ‐ trans pairs of stilbene imines proceeds stereospecifically irrespective of the kind of mono activation by the phenylsulfonyl group ( 1 ), by the benzoyl group ( 2 ), or by protonation of the aziridine base ( 3 ). In accordance with complete Walden inversion, the sole product from the cis isomer is always a diastereomer of the sole product from the trans isomer. The diastereomers obtained from 3 are correlated with the respective diastereomers obtained from 2 .