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cis,cis-Spiro[4.4]nonane-1,6-diol: A new chiral auxiliary for the asymmetric Diels-Alder reaction

✍ Scribed by James A. Nieman; Brian A. Keay

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 389 KB
Volume: 7
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(96)00459-4

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✦ Synopsis

The use ofa mono-pivalate mono-acrylate bis-ester of (+)-lS,5S,6S-spirol4.4]nonane-l,6diol in an asymmetric Dieis-Alder reaction with cyclopentadiene (2 equiv. BCI3, -85°C, CH2C12) provided the expected endo bicyclo adduct in >97% de. Iodolactonization of the bicyclo adduct provided the (+)-lactune (5) with a 1S,4S,6S,8R,9S configuration (97% ee). The de's obtained from using various types and amounts of Lewis acids, and both chiral and racemic bis-esters in the Dieis-Alder reaction with cyciopentadiene are also reported.

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