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Synlett 2000; 2000(1): 92-94
DOI: 10.1055/s-2000-6434
DOI: 10.1055/s-2000-6434
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
A Silicon-Mediated Domino Approach to Pyrrolidine- and Piperidine-2,3-diones
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synlett/200001/lookinside/thumbnails/10.1055-s-2000-6434-1.jpg)
Lithiated silylthioacetals 1 react with ω-bromoalkyl isocyanates 2 via addition to the isocyanate, a 1,3-silyl shift and ring-closure by bromide displacement to give lactams 6. The latent α-oxo group can be liberated by thioacetal cleavage with hypervalent iodine to yield diones 10.
silyl-stabilized carbanions - ω-bromoisocyanates - thioacetals - hypervalent iodine