Premium
Reagent‐Controlled Switching of 5‐ exo to 6‐ endo Cyclizations in Epoxide Openings
Author(s) -
Morimoto Yoshiki,
Nishikawa Yoshihiro,
Ueba Chigusa,
Tanaka Takeshi
Publication year - 2006
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/anie.200503143
Subject(s) - epoxide , nitromethane , reagent , substrate (aquarium) , trifluoromethanesulfonate , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , oceanography , geology
Against the rules : The switching of the usual 5‐ exo cyclizations of epoxide substrates to the 6‐ endo mode, which goes against Baldwin's rule, is demonstrated by treating bishomoepoxy alcohols with triisopropylsilyl triflate (TIPSOTf) in nitromethane (see scheme). This method is different to those previously reported in which elaborate modifications of the epoxide substrate are required to attain 6‐ endo cyclization.