Organometallic ring-opening reactions of N-acyl and N-alkoxycarbonyl lactams. Synthesis of cyclic imines

…, D Savoia, A Umani-Ronchi

Index: Giovannini, Arianna; Savoia, Diego; Umani-Ronchi, Achille Journal of Organic Chemistry, 1989 , vol. 54, # 1 p. 228 - 234

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Citation Number: 123

Abstract

The reactions of hexyl-and phenylmagnesium bromides with N-acyl and N-alkoxycarbonyl lactams in tetrahydrofuran at-78 OC have been performed to determine the factors affecting the regioselectivity. N-Pivaloyl y-and 6-lactams undergo the ring-opening reactions with both Grignard reagents, whereas on the N-benzoyl y-lactam a complete selectivity is achieved only with phenylmagnesium bromide. The N-Cbz y-and d-lactams preferentially react at ...