4.6 Article

Stereospecific anti S(E)2 ' fluorination of allenylsilanes: synthesis of enantioenriched propargylic fluorides

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 6, Issue 10, Pages 1731-1733

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/b803888k

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The electrophilic fluorodesilylation of enantioenriched allenylsilanes proceeds with efficient transfer of chirality. The silylation - fluorination of propargylic alcohols occurs with overall retention of stereochemistry, a result consistent with a stereospecific anti S(E)2' mechanism for the fluorination step.

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