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Catalytic Asymmetric Total Synthesis of Chimonanthine, Folicanthine, and Calycanthine through Double Michael Reaction of Bisoxindole
Author(s) -
Mitsunuma Harunobu,
Shibasaki Masakatsu,
Kanai Motomu,
Matsunaga Shigeki
Publication year - 2012
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.201201132
Subject(s) - stereocenter , vicinal , catalysis , steric effects , michael reaction , chemistry , benzoic acid , combinatorial chemistry , organic chemistry , stereochemistry , enantioselective synthesis
Direct access : Sterically hindered vicinal quaternary carbon stereocenters were constructed by catalytic enantio‐ and diastereoselective double Michael reaction, providing straightforward access to dimeric hexahydropyrroloindole alkaloids. A Mn(4‐fluorobenzoate) 2 /Schiff base complex and a Mg(OAc) 2 /benzoic acid system were used as catalysts.