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Synlett 2001; 2001(7): 1079-1091
DOI: 10.1055/s-2001-15134
DOI: 10.1055/s-2001-15134
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© 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.
The Silyloxy-Cope Rearrangement of Syn-Aldol Products: Evolution of a Powerful Synthetic Strategy
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2001 (online)
![](https://www.thieme-connect.de/media/synlett/200107/lookinside/thumbnails/10.1055-s-2001-15134-1.jpg)
Enantiomerically pure 1,5-hexadienes incorporated into a silylated aldol structure undergo rapid, clean, high-yielding and highly stereoselective Cope rearrangements. The 7-oxo-2-enimides thus obtained are formally the products of a γ-1,4-selective addition of a metal dienolate to an α,β-unsaturated aldehyde - a transformation which current methodology can not accomplish directly and stereoselectively. They have proved to be very useful synthetic intermediates en route to highly substituted oxygen and nitrogen heterocycles, functionalized cyclohexanes, and 1,3,5,‥-polyol chains.
aldol products - asymmetric synthesis - Cope rearrangement - cyclohexanes - heterocycles - polyols