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Enantioselective ?-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis.

ABSTRACT: The enantioselective ?-arylation of aldehydes has been accomplished using diaryliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable ?-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.

SUBMITTER: Allen AE

PROVIDER: S-EPMC3082494 | biostudies-literature | 2011 Mar

REPOSITORIES: biostudies-literature

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Enantioselective α-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis.

Allen Anna E AE MacMillan David W C DW

Journal of the American Chemical Society 20110309 12

The enantioselective α-arylation of aldehydes has been accomplished using diaryliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable α-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and to ...[more]

PMID: 21388207

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