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Single and double stereoselective fluorination of (E)-allylsilanes.

ABSTRACT: Acyclic allylic monofluorides were prepared by electrophilic fluorination of branched (E)-allylsilanes with Selectfluor. These reactions proceeded with efficient transfer of chirality from the silylated to the fluorinated stereocentre. Upon double fluorination, an unsymmetrical ethyl syn-2,5-difluoroalk-3-enoic ester was prepared, the silyl group acting as an anti stereodirecting group for the two C-F bond forming events.

SUBMITTER: Sawicki M

PROVIDER: S-EPMC2151074 | biostudies-literature | 2007 Oct

REPOSITORIES: biostudies-literature

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Single and double stereoselective fluorination of (E)-allylsilanes.

Sawicki Marcin M Kwok Angela A Tredwell Matthew M Gouverneur Véronique V

Beilstein journal of organic chemistry 20071025

Acyclic allylic monofluorides were prepared by electrophilic fluorination of branched (E)-allylsilanes with Selectfluor. These reactions proceeded with efficient transfer of chirality from the silylated to the fluorinated stereocentre. Upon double fluorination, an unsymmetrical ethyl syn-2,5-difluoroalk-3-enoic ester was prepared, the silyl group acting as an anti stereodirecting group for the two C-F bond forming events. ...[more]

PMID: 17961218

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