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Issue 10, 2008
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Stereospecific anti SE2′ fluorination of allenylsilanes: synthesis of enantioenriched propargylic fluorides

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Abstract

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 SE2′ mechanism for the fluorination step.

Graphical abstract: Stereospecific anti SE2′ fluorination of allenylsilanes: synthesis of enantioenriched propargylic fluorides

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Publication details

The article was received on 06 Mar 2008, accepted on 20 Mar 2008 and first published on 03 Apr 2008


Article type: Communication
DOI: 10.1039/B803888K
Citation: Org. Biomol. Chem., 2008,6, 1731-1733
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    Stereospecific anti SE2′ fluorination of allenylsilanes: synthesis of enantioenriched propargylic fluorides

    L. Carroll, S. McCullough, T. Rees, T. D. W. Claridge and V. Gouverneur, Org. Biomol. Chem., 2008, 6, 1731
    DOI: 10.1039/B803888K

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