Temperature Effects in Asymmetric Dihydroxylation: Evidence for a Stepwise Mechanism | Zendy

Göbel Thomas | Zendy; Sharpless K. Barry | Zendy

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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.

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