Highly Diastereo‐ and Enantioselective Mannich Reactions of Synthetically Flexible Ketimines with Secondary Amine Organocatalysts | Zendy

Kano Taichi | Zendy; Song Sunhwa | Zendy; Kubota Yasushi | Zendy; Maruoka Keiji | Zendy

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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).

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