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Highly Diastereo‐ and Enantioselective Mannich Reactions of Synthetically Flexible Ketimines with Secondary Amine Organocatalysts
Author(s) -
Kano Taichi,
Song Sunhwa,
Kubota Yasushi,
Maruoka Keiji
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.201107375
Subject(s) - enantioselective synthesis , stereoselectivity , amine gas treating , mannich reaction , chemistry , carbon fibers , selectivity , organic chemistry , combinatorial chemistry , organocatalysis , catalysis , computer science , algorithm , composite number
High selectivity : A highly diastereo‐ and enantioselective Mannich reaction between a synthetically flexible ketimine and aldehydes has been developed. The syn ‐ or anti ‐Mannich products contain tetrasubstituted chiral carbon centers and were obtained with almost complete stereoselectivity by using either L ‐proline or an axially chiral aminosulfonamide, respectively, as the catalyst (see scheme, Tf=trifluoromethanesulfonyl).