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ChemInform Abstract: Intramolecular Diels-Alder Reactions of Alkenylboranes - A Stereoselective Route to Functionalized Bicyclo(4.3.0)nonenes.

✍ Scribed by R. A. BATEY; D. LIN; A. WONG; C. L. S. HAYHOE

Publisher: John Wiley and Sons
Year: 2010
Weight: 30 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199736047

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✦ Synopsis

Intramolecular Diels-Alder Reactions of Alkenylboranes -A Stereoselective Route to Functionalized Bicyclo(4.3.0)nonenes.

-An optimized methodology for the synthesis of trans-fused title bicycles is presented using a three-step one-pot strategy. In situ formed alkenylboranes undergo stereoselective intramolecular Diels-Alder reaction in the presence of butylated hydroxytoluene as radical inhibitor to give alkylboranes, which upon oxidation yield the desired endo addition products.

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