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Synlett 2001; 2001(7): 1079-1091
DOI: 10.1055/s-2001-15134
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The Silyloxy-Cope Rearrangement of Syn-Aldol Products: Evolution of a Powerful Synthetic Strategy

Christoph Schneider*
  • *Institut für Organische Chemie der Georg-August-Universität, Tammannstr. 2, 37077 Göttingen, Germany; Fax + 49-551-39 96 60; E-mail: cschnei1@gwdg.de
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Publication Date:
31 December 2001 (online)

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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