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Asymmetric bisboranes as bidentate catalysts for carbonyl substrates.

ABSTRACT: A new class of C(2) symmetric bisoxazaborolidinone compounds is described which exhibits bidentate binding to carbonyl substrates. Using the Diels-Alder reaction as a model system, the catalytic activity of these bis-Lewis acids is probed. Reaction rates and selectivities are observed that are higher than the corresponding mono-Lewis acids. This novel system offers a potentially powerful new approach to asymmetric Lewis acid catalysis.

SUBMITTER: Rodriguez AA

PROVIDER: S-EPMC2662717 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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Asymmetric bisboranes as bidentate catalysts for carbonyl substrates.

Rodriguez Andrew A AA Zhao Carrie C Shea Kenneth J KJ

Organic letters 20090201 3

A new class of C(2) symmetric bisoxazaborolidinone compounds is described which exhibits bidentate binding to carbonyl substrates. Using the Diels-Alder reaction as a model system, the catalytic activity of these bis-Lewis acids is probed. Reaction rates and selectivities are observed that are higher than the corresponding mono-Lewis acids. This novel system offers a potentially powerful new approach to asymmetric Lewis acid catalysis. ...[more]

PMID: 19175350

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