Solvent‐Dependent Enantiodivergent Mannich‐Type Reaction: Utilizing a Conformationally Flexible Guanidine/Bisthiourea Organocatalyst | Zendy

Sohtome Yoshihiro | Zendy; Tanaka Shinji | Zendy; Takada Keisuke | Zendy; Yamaguchi Takahisa | Zendy; Nagasawa Kazuo | Zendy

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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.

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