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Asymmetric Bromolactonization Catalyzed by a C 3 ‐Symmetric Chiral Trisimidazoline
Author(s) -
Murai Kenichi,
Matsushita Tomoyo,
Nakamura Akira,
Fukushima Shunsuke,
Shimura Masato,
Fujioka Hiromichi
Publication year - 2010
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.201005409
Subject(s) - enantioselective synthesis , catalysis , substrate (aquarium) , chemistry , stereochemistry , organocatalysis , ion , combinatorial chemistry , organic chemistry , oceanography , geology
A productive alliance : In an enantioselective organocatalytic bromolactonization of 5‐substituted hex‐5‐enoic acids (see scheme), it appears that the formation of an ion pair through interaction of the trisimidazoline catalyst 1 with the substrate both creates a chiral environment and promotes the cyclization by activating the carboxylic acid. DBDMH=1,3‐dibromo‐5,5‐dimethylhydantoin.