Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 4, Pages 619-623Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200700504
Keywords
asymmetric reduction; S-chiral bissulfinamide; ketimines; organocatalysis
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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 (HSiCl3) to reduce N-arylketimines. A plausible mechanism involving two molecules of the monosulfinamde catalyst for the activation of HSiCl3 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.
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