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Enantioselective Synthesis of Hydrobenzofuranones Using an Asymmetric Desymmetrizing Intramolecular Stetter Reaction of Cyclohexadienones.

ABSTRACT: A series of cyclohexadienones were synthesized by dearomatization of phenols followed by Dess-Martin oxidation. Asymmetric intramolecular Stetter reactions of these substrates provide hydrobenzofuranones in good to excellent yields and excellent stereoselectivities. Up to three stereocenters as well as quaternary stereocenter are formed from polysubstituted substrates. A scale up experiment demonstrates the utility of this transformation.

SUBMITTER: Liu Q

PROVIDER: S-EPMC2709411 | biostudies-literature | 2007

REPOSITORIES: biostudies-literature

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Enantioselective Synthesis of Hydrobenzofuranones Using an Asymmetric Desymmetrizing Intramolecular Stetter Reaction of Cyclohexadienones.

Liu Qin Q Rovis Tomislav T

Organic process research & development 20070101 3

A series of cyclohexadienones were synthesized by dearomatization of phenols followed by Dess-Martin oxidation. Asymmetric intramolecular Stetter reactions of these substrates provide hydrobenzofuranones in good to excellent yields and excellent stereoselectivities. Up to three stereocenters as well as quaternary stereocenter are formed from polysubstituted substrates. A scale up experiment demonstrates the utility of this transformation. ...[more]

PMID: 19603085

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