Catalytic Asymmetric Mannich‐Type Reaction of  N ‐Alkylidene‐α‐Aminoacetonitrile with Ketimines | Zendy

Lin Shaoquan | Zendy; Kawato Yuji | Zendy; Kumagai Naoya | Zendy; Shibasaki Masakatsu | Zendy

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Catalytic Asymmetric Mannich‐Type Reaction of N ‐Alkylidene‐α‐Aminoacetonitrile with Ketimines

Author(s) -

Lin Shaoquan,

Kawato Yuji,

Kumagai Naoya,

Shibasaki Masakatsu

Publication year - 2015

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.201412377

Subject(s) - stereocenter , chemistry , catalysis , vicinal , lewis acids and bases , stereoselectivity , enantioselective synthesis , combinatorial chemistry , brønsted–lowry acid–base theory , organic chemistry , aldol reaction , organocatalysis

Optically active vicinal diamines are versatile chiral building blocks in organic synthesis. A soft Lewis acid/hard Brønsted base cooperative catalyst allows for an efficient stereoselective coupling of N ‐alkylidene‐α‐aminoacetonitrile and ketimines to access this class of compounds bearing consecutive tetra‐ and trisubstituted stereogenic centers. The strategic use of a soft Lewis basic thiophosphinoyl group for ketimines is the key to promoting the reaction, and aliphatic ketimines serve as suitable substrates with as little as 3 mol % catalyst loading.

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