Selective nucleophilic addition reactions of alkyllithium reagents with N-(trimethylsilyl) lactams. Synthesis of cyclic ketimines

…, SN Bharathi, T Katsuhira, AA Bravo

Index: Hua, Duy H.; Miao, Shou Wu; Bharathi, S. Narasimha; Katsuhira, Takeshi; Bravo, Ana A. Journal of Organic Chemistry, 1990 , vol. 55, # 11 p. 3682 - 3684

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Citation Number: 72

Abstract

In our studies of the enantioselective synthesis of alkaloids via chiral a-sulfinyl ketimines,'p2 cyclic ketimines of various ring size and containing diverse substituents, eg la-h, were required. Four methods have been reported for the synthesis of cyclic ketimines:(1) additions of organolithium reagents to N-vinyllactams?(2) acid-catalyzed rearrangement of tertiary azides:(3) palladium-catalyzed oxidation of amino alkenes? and (4) additions of ...