Synlett

A Silicon-Mediated Domino Approach to Pyrrolidine-and Piperidine-2, 3-diones

A Jung, O Koch, M Ries, E Schaumann

Index: Jungf, Alexander; Koch, Oliver; Ries, Monika; Schaumann, Ernst Synlett, 2000 , # 1 p. 92 - 94

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Citation Number: 5

Abstract

Abstract: Lithiated silylthioacetals 1 react with w-bromoalkyl isocyanates 2 via addition to the isocyanate, a 1, 3-silyl shift and ringclosure by bromide displacement to give lactams 6. The latent aoxo group can be liberated by thioacetal cleavage with hypervalent iodine to yield diones 10. Key words: silyl-stabilized carbanions, w-bromoisocyanates, thioacetals, hypervalent iodine

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