Premium
Entropy‐Controlled Catalytic Asymmetric 1,4‐Type Friedel–Crafts Reaction of Phenols Using Conformationally Flexible Guanidine/Bisthiourea Organocatalyst
Author(s) -
Sohtome Yoshihiro,
Shin Bongki,
Horitsugi Natsuko,
Takagi Rika,
Noguchi Keiichi,
Nagasawa Kazuo
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.201003172
Subject(s) - friedel–crafts reaction , chemistry , phenols , catalysis , guanidine , type (biology) , organic chemistry , combinatorial chemistry , ecology , biology
Soft and weak cooperation : Conformationally flexible organic compounds were found to promote the title transformation. These “soft” organocatalysts, which are able to control processes through the differential activation entropies (ΔΔ S ≠ S − R ) of the reactive intermediates, lead to high stereoselectivities without the requirement of fine‐tuning the reaction temperatures (see scheme).