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One-pot catalytic asymmetric synthesis of pyranones.

ABSTRACT: Enantioenriched pyranones are important intermediates in the synthesis of natural products and the generation of compound libraries. A one-pot method for their synthesis is outlined. Catalytic asymmetric alkylation of 2-furfurals in the presence of catalytic (-)-MIB generates enantioenriched furyl zinc alkoxides. Addition of water/THF followed by NBS results in formation of pyranones with ee's >90% and yields between 46-77%.

SUBMITTER: Cheng K

PROVIDER: S-EPMC2709820 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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One-pot catalytic asymmetric synthesis of pyranones.

Cheng Kevin K Kelly Ann Rowley AR Kohn Rachel A RA Dweck Jessica F JF Walsh Patrick J PJ

Organic letters 20090601 12

Enantioenriched pyranones are important intermediates in the synthesis of natural products and the generation of compound libraries. A one-pot method for their synthesis is outlined. Catalytic asymmetric alkylation of 2-furfurals in the presence of catalytic (-)-MIB generates enantioenriched furyl zinc alkoxides. Addition of water/THF followed by NBS results in formation of pyranones with ee's >90% and yields between 46-77%. ...[more]

PMID: 19456165

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