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Stereospecific Suzuki cross-coupling of alkyl alpha-cyanohydrin triflates.

ABSTRACT: Scalemic alpha-cyanohydrin triflates undergo Pd-catalyzed cross-coupling with aryl, heteroaryl, and vinyl boronic acids under mild conditions. Coupling proceeds with complete inversion of configuration at the stereogenic carbon. The resultant nitrile can be easily converted into a variety of alternative functional groups of value in organic synthesis and thus achieves a higher level of molecular complexity than the products of traditional Suzuki reactions.

SUBMITTER: He A

PROVIDER: S-EPMC2893341 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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Stereospecific Suzuki cross-coupling of alkyl alpha-cyanohydrin triflates.

He Anyu A Falck J R JR

Journal of the American Chemical Society 20100301 8

Scalemic alpha-cyanohydrin triflates undergo Pd-catalyzed cross-coupling with aryl, heteroaryl, and vinyl boronic acids under mild conditions. Coupling proceeds with complete inversion of configuration at the stereogenic carbon. The resultant nitrile can be easily converted into a variety of alternative functional groups of value in organic synthesis and thus achieves a higher level of molecular complexity than the products of traditional Suzuki reactions. ...[more]

PMID: 20121273

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