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Solvent‐Dependent Enantiodivergent Mannich‐Type Reaction: Utilizing a Conformationally Flexible Guanidine/Bisthiourea Organocatalyst
Author(s) -
Sohtome Yoshihiro,
Tanaka Shinji,
Takada Keisuke,
Yamaguchi Takahisa,
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.201005109
Subject(s) - chemistry , organocatalysis , adduct , solvent , catalysis , guanidine , organic chemistry , mannich reaction , enthalpy , kinetic control , enantioselective synthesis , thermodynamics , physics
Flex control : Malonate and tert ‐butoxycarbonyl (Boc)‐protected imines react in the presence of the flexible catalyst 1 to furnish the S or the R adduct depending upon the solvent used. Kinetic analyses in this enantiodivergent organocatalysis show that enthalpy–entropy compensation explains this behavior.