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Catalytic enantioselective cyclization and C3-fluorination of polyenes.

ABSTRACT: (Xylyl-phanephos)Pt(2+) in combination with XeF(2) mediates the consecutive diastereoselective cation-olefin cyclization/fluorination of polyene substrates. Isolated yields were typically in the 60-69% range while enantioselectivities reached as high as 87%. The data are consistent with a stereoretentive fluorination of a P(2)Pt-alkyl cation intermediate.

SUBMITTER: Cochrane NA

PROVIDER: S-EPMC3552331 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Catalytic enantioselective cyclization and C3-fluorination of polyenes.

Cochrane Nikki A NA Nguyen Ha H Gagne Michel R MR

Journal of the American Chemical Society 20130108 2

(Xylyl-phanephos)Pt(2+) in combination with XeF(2) mediates the consecutive diastereoselective cation-olefin cyclization/fluorination of polyene substrates. Isolated yields were typically in the 60-69% range while enantioselectivities reached as high as 87%. The data are consistent with a stereoretentive fluorination of a P(2)Pt-alkyl cation intermediate. ...[more]

PMID: 23282101

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