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Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins.

ABSTRACT: A method for asymmetric alkyl-alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with alkylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components.

SUBMITTER: Owston NA

PROVIDER: S-EPMC2929007 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins.

Owston Nathan A NA Fu Gregory C GC

Journal of the American Chemical Society 20100901 34

A method for asymmetric alkyl-alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with alkylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components. ...[more]

PMID: 20701271

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