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Rationally‐Designed S‐ Chiral Bissulfinamides as Highly Enantioselective Organocatalysts for Reduction of Ketimines
Author(s) -
Pei Dong,
Zhang Yu,
Wei Siyu,
Wang Meng,
Sun Jian
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700504
Subject(s) - enantioselective synthesis , chemistry , trichlorosilane , organocatalysis , catalysis , combinatorial chemistry , lewis acids and bases , substrate (aquarium) , organic chemistry , stereochemistry , oceanography , geology , silicon
We recently reported the first example of S ‐chiral organocatalysts, that are highly efficient and enantioselective in substoichometric amounts, and which use a chiral monosulfinamide group as Lewis base to activate trichlorosilane (HSiCl 3 ) to reduce N ‐arylketimines. A plausible mechanism involving two molecules of the monosulfinamde catalyst for the activation of HSiCl 3 prompted us to design S ‐chiral bissulfinamides as new catalysts. We herein describe our findings that an easily prepared S ‐chiral bissulfinamide bearing a five‐methylene linkage not only inherited the excellent substrate generality from the monosulfinamide catalysts, but also exhibited further improved enantioselectivity.