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Ruthenium‐Catalyzed Asymmetric Propargylic Substitution Reactions of Propargylic Alcohols with Acetone
Author(s) -
Inada Youichi,
Nishibayashi Yoshiaki,
Uemura Sakae
Publication year - 2005
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.200502981
Subject(s) - ruthenium , acetone , enantioselective synthesis , substitution (logic) , catalysis , chemistry , ligand (biochemistry) , alkylation , selectivity , substitution reaction , organic chemistry , medicinal chemistry , combinatorial chemistry , computer science , biochemistry , receptor , programming language
Enantioselective propargylic substitution reactions of propargylic alcohols with acetone catalyzed by a diruthenium complex gives the propargylic alkylated products in good yields with up to 82 % ee. A π–π interaction of phenyl rings between the ligand and allenylidene moieties is considered to play a crucial role in achieving such a high selectivity (see scheme; Cp*=pentamethylcyclopentadiene).