Addition of amino amides to vinyl vicinal tricarbonyls. Formation of tricyclic 3-azadethiacephams

HH Wasserman, SL Henke, E Nakanishi…

Index: Wasserman, Harry H.; Henke, Susan L.; Nakanishi, Eiji; Schulte, Gayle Journal of Organic Chemistry, 1992 ,  vol. 57,  # 9  p. 2641 - 2645

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Citation Number: 20

Abstract

Amino amides react as trinucleophiles with vinyl vicinal tricarbonyl esters. Reaction of the primary amino group takes place at the@-position of the a,@-unsaturated ketone along with addition to the central carbonyl group. In a third-stage reaction, the amide residue adds to the iminium ion formed from the intermediate carbinolamine. The resulting product is a bicyclic or tricyclic (acylamino) py-rrolidone carboxylate. A novel tricyclic 3- ...