The Journal of Organic Chemistry

Formation, electrophilic substitution, and formal 3+ 2 cyclization of (2-carbamoylallyl) lithium reagents

P Beak, KD Wilson

Index: Beak, Peter; Wilson, Kenneth D. Journal of Organic Chemistry, 1986 , vol. 51, # 24 p. 4627 - 4639

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Citation Number: 20

Abstract

Directed p'-lithiations of a,@-unsaturated amides and reactions of the resulting (2- carbamoylally1) lithium reagents with electrophiles are reported. Treatment of (E)-N, N- diisopropyl-2-methyl-2-butenamide(5) provides [(E)-2-(N, N-diisopropylcarbamoyl)-3- methylallyl] lithium (6), which has retained the double bond geometry of 5 and undergoes reaction with a variety of electrophiles to provide the@-and p'-substituted products 7-20. ...