TITLE:
Recyclable Cyclohexanediamine Derivatives as Organocatalysts: Organocatalytic Reduction with Trichlorosilane and Aldol Reaction
AUTHORS:
Yuya Tanimura, Kaori Ishimaru
KEYWORDS:
Aldol Reaction; Cyclohexanediamine; Organocatalysis; Recyclable; Reduction
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.3 No.4,
December
27,
2013
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.