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Diastereoface‐Selective Epoxidations: Dependency on the Reagent Electrophilicity
Author(s) -
Fehr Charles
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980918)37:17<2407::aid-anie2407>3.0.co;2-w
Subject(s) - electrophile , steric effects , reagent , toluene , chemistry , substrate (aquarium) , dependency (uml) , computational chemistry , organic chemistry , computer science , catalysis , geology , oceanography , software engineering
Substrate‐imposed steric constraints can be overriden by the pronounced preference of strong peracids for epoxidation on the π face, which has the highest electron density. For example, the syn : anti ratio for reaction (1) with CF 3 CO 3 H in CH 2 Cl 2 is 82:18, that with CH 3 CO 3 H in toluene is 3:97.