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Temperature Effects in Asymmetric Dihydroxylation: Evidence for a Stepwise Mechanism
Author(s) -
Göbel Thomas,
Sharpless K. Barry
Publication year - 1993
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.199313291
Subject(s) - dihydroxylation , mechanism (biology) , enantiomer , chemistry , reaction mechanism , enantiomeric excess , enantioselective synthesis , computational chemistry , stereochemistry , organic chemistry , catalysis , philosophy , epistemology
For more than 50 years, the accepted opinion was that the dihydroxylation of olefins with OsO 4 proceeded by a concerted mechanism [Eq. (a)]. However, if the influence of the reaction temperature on the enantiomeric excesses in asymmetric dihydroxylations is studied, Eyring plots are obtained with inversion points, which is consistent with a stepwise mechanism.