Enantioselective Strecker Reaction Promoted by Chiral N-Oxides

Bo Liu; Xiaoming Feng; Fuxue Chen; Guolin Zhang; Xin Cui; Yaozhong Jiang

doi:10.1055/s-2001-17472

Synlett 2001; 2001(10): 1551-1554
DOI: 10.1055/s-2001-17472

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Enantioselective Strecker Reaction Promoted by Chiral N-Oxides

Bo Liu^* , Xiaoming Feng, Fuxue Chen, Guolin Zhang, Xin Cui, Yaozhong Jiang

^*The Faculty of Chemistry, Sichuan University, Chengdu 610064, China; Fax + 86(28)5 41 29 07; E-mail: xm9feng@china.com

Abstract

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The asymmetric Strecker reaction of aldimines and trimethylsilyl cyanide promoted by 1 equivalent of chiral N-oxide affords the corresponding α-amino nitriles with enantioselectivities of up to 73% most effectively for electron-deficient aldimines under mild reaction conditions. Two new resolving methods and one new synthetic methodology were developed to obtain three novel chiral N-oxides.

chiral N-oxides - asymmetric synthesis - nucleophilic additions - imines - optically active amino nitriles

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