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Palladium(0)-catalyzed synthesis of chiral ene-allenes using alkenyl trifluoroborates.

ABSTRACT: Enantioenriched allenes serve as chiral transfer reagents, making them attractive synthetic targets. Herein, the synthesis of enantioenriched allenes utilizing a Pd(0)-catalyzed cross-coupling reaction of propargylic carbonates and phosphates with alkenyl trifluoroborates is reported. Di-, tri-, and tetrasubstituted allenes were synthesized in moderate to high optical yields. Several racemic allenes possessing various functional groups were also synthesized.

SUBMITTER: Molander GA

PROVIDER: S-EPMC2504514 | biostudies-literature | 2006 Feb

REPOSITORIES: biostudies-literature

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Palladium(0)-catalyzed synthesis of chiral ene-allenes using alkenyl trifluoroborates.

Molander Gary A GA Sommers Erin M EM Neufeldt Sharon R SR

The Journal of organic chemistry 20060201 4

Enantioenriched allenes serve as chiral transfer reagents, making them attractive synthetic targets. Herein, the synthesis of enantioenriched allenes utilizing a Pd(0)-catalyzed cross-coupling reaction of propargylic carbonates and phosphates with alkenyl trifluoroborates is reported. Di-, tri-, and tetrasubstituted allenes were synthesized in moderate to high optical yields. Several racemic allenes possessing various functional groups were also synthesized. ...[more]

PMID: 16468806

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