H. Ishitani, Susumu Komiyama, and Yoshiki Hasegawa
Jan 25, 2000
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Journal
Journal of the American Chemical Society
Abstract
Catalytic enantioselective Strecker-type reactions of aldimines with tributyltin cyanide (Bu3SnCN) proceeded smoothly in the presence of a novel chiral zirconium catalyst. High levels of enantioselectivities in the synthesis of α-amino nitrile derivatives with wide substrate generality were obtained via these reactions. In addition, hydrogen cyanide (HCN) was successfully used instead of Bu3SnCN as the cyanide source. Catalytic asymmetric Strecker amino acid synthesis starting from achiral aldehydes, amines, and HCN using a chiral zirconium catalyst has also been achieved. The three-component asymmetric process reported here significantly improves upon the original Strecker reaction, and has advantages over previous reactions using unstable imines (Schiff bases) as starting materials. Moreover, high yields and enantioselectivities have been obtained even in the reactions using aliphatic aldehydes, and both enantiomers of various types of α-amino acid derivatives can be prepared. As demonstrations to show ...