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Synlett 1997; 1997(7): 815-817
DOI: 10.1055/s-1997-5748
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Stereodivergent Synthesis of Enantiopure Tetrahydropyrans via the Silyloxy-Cope Rearrangement of Chiral Aldol Products

Christoph Schneider*
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany, Fax: +49-551-399660; e-mail: cschnei1@gwdg.de
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Publication Date:
31 December 2000 (online)

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A stereoselective synthesis of highly substituted and enantiopure tetrahydropyrans from chiral 7-hydroxy-2-alkenoic imides and esters is described. Depending on the carboxylic acid derivative the base-induced cyclization is kinetically or thermodynamically controlled to deliver either tetrahydropyran stereoisomer selectively.

tetrahydropyrans - intramolecular conjugate addition - Cope rearrangement - aldol products - natural products

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