Abstract
Reduction of ketimine with trichlorosilane was carried out using bisformamide catalyst 1a derived from cyclohexanediamine to give the corresponding product in 81% yield with 39% ee. Deprotection of the formyl groups of the catalysts 1 gave the corresponding diamines 2 which were utilized in aldol reaction of acetone with 4-nitrobenzaldehyde. The reaction using 2b in brine afforded the aldol adduct in 81% yield with 29% ee.
Highlights
The field of organocatalysis has been rapidly growing in recent years because the reactions have evolved into a non-metal, abundant, and environmentally benign methodology [1,2,3]
We have succeeded in asymmetric allylation reaction of arylaldehydes with allyltrichlorosilane using bisformamide organocatalysts 1 (Figure 1) which were prepared from cyclohexanediamine [4,5]
We thought that the catalysts 1 would be useful for other reactions such as reduction of ketimines with trichlorosilane because trichlorosilane was activated by Lewis bases [6,7]
Summary
The field of organocatalysis has been rapidly growing in recent years because the reactions have evolved into a non-metal, abundant, and environmentally benign methodology [1,2,3]. We thought that the catalysts 1 would be useful for other reactions such as reduction of ketimines with trichlorosilane because trichlorosilane was activated by Lewis bases [6,7]. The diamine catalysts 2 could be converted to the bisformamide catalyst 1 by protection of amino groups, showing that both catalysts 1 and 2 were converted to each other. This recycle system of the catalysts has not been reported yet, our novel design. We report the recyclable organocatalysts derived from cyclohexanediamine and application for reduction of ketimine and aldol reaction
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