American Chemical Society
jo062215i_si_001.pdf (6.22 MB)

Organocatalysis with a Fluorous Tag:  Asymmetric Reduction of Imines with Trichlorosilane Catalyzed by Amino Acid-Derived Formamides

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journal contribution
posted on 2007-02-16, 00:00 authored by Andrei V. Malkov, Marek Figlus, Sigitas Stončius, Pavel Kočovský
Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by N-methylvaline-derived Lewis-basic formamides 3ad with high enantioselectivity (≤95% ee) and low catalyst loading (1−5 mol %) at room temperature in toluene. Appending a fluorous tag, as in 5ac, simplifies the isolation procedure, while preserving high enantioselectivity (≤92% ee).