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Enantioselective construction of spiro{cyclopropane-14′-bicyclo[3.3.0]oct-1-en-3-ones}

✍ Scribed by Andreas Stolle; Heike Becker; Jacques Salaün; Armin de Meijere

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 307 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73225-4

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✦ Synopsis

Imramolccular Paoson-Khand reactions of M-enynes 3a-c with a methylenecyclopropane terminator and a cbii acetal moiety adjacent to the triple bond gave spiro(cyclopropaae-l,4'-bicyclo[3.3.0]oct-l-en-3-ones) 5a-c in good yields with a diaste~lcctivity of up to 6.411. 'Ihe major diastenxmer of 5b was converted to enantiomerically pore bicyclo[3.3.O]octane-3&dione 8, which showed a negative peak at 287 nm in the CD curve, consistent with an assumed (SR) configuration.

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