Chemical and pharmaceutical bulletin

The effects of Lewis acid on the 1, 3-dipolar cycloaddition reaction of C-arylaldonitrones with alkenes.

T Shimizu, M Ishizaki, N Nitada

Index: Shimizu, Tomio; Ishizaki, Masaya; Nitada, Nobuo Chemical and Pharmaceutical Bulletin, 2002 , vol. 50, # 7 p. 908 - 921

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Citation Number: 16

Abstract

The regio-and stereoselectivity of the 1, 3-dipolar cycloaddition reactions of C-aryl-N- alkylaldonitrones (1a—e) with some alkenes were found to be affected significantly by the addition of Lewis acid. The rate of the reaction was also affected by adding the Lewis acid. In the reactions using allyl alcohol as a dipolarophile an addition of Lewis acid caused a remarkable acceleration of the reaction and a great change in the stereoselectivity. In the ...