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Preparation and Detection of Enantiomerically Enriched and Configurationally Stable α‐Thioalkyllithium Compounds
Author(s) -
Kaiser Bernd,
Hoppe Dieter
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199503231
Subject(s) - carbanion , steric effects , electrophile , chemistry , electrophilic substitution , deuterium , computational chemistry , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics
Sterically demanding and carbanion‐stabilizing substituents like SiMe 3 raise the barrier to the configurational inversion of α‐thioalkyllithium compounds. With such substituents these compounds can undergo, for example, electrophilic substitution [Eq. (a)] without changes in configuation. Experiments with deuterated compounds proved that alkyllithium intermediates from primary S ‐alkylthiocarbamates are typically not configurationally stable.