The Journal of Organic Chemistry

Stereocontrolled synthesis of N-vinyl-, N-(1'-propenyl)-, and N-unsubstituted-. beta.-lactams from 2-aza-1, 3-butadienes via the Staudinger reaction

GI Georg, P He, J Kant, ZJ Wu

Index: Georg, Gunda I.; He, Ping; Kant, Joydeep; Wu, Zhi-jun Journal of Organic Chemistry, 1993 , vol. 58, # 21 p. 5771 - 5778

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Citation Number: 36

Abstract

2-Aza-1, 3-butadienes 2 and 5 were synthesized in good yields and on a large scale. Reaction of 2 and 5 with acid chlorides in the presence of triethylamine (Staudinger reaction) resulted in the highyielding formation of N-vinyl-and N-(1'-propenyl)-8-lactams. Excellent cis-stereoselectivity was observed in the reaction of a-aza-l, &butadienes 2 and 5 with Bose-Evans ketenes and Sheehan ketenes, whereas reaction with a Moore ketene ...