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

Laurence Carroll; Samantha McCullough; Tom Rees; Timothy D. W. Claridge; Véronique Gouverneur

doi:10.1039/B803888K

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Stereospecific anti S_E2′ fluorination of allenylsilanes: synthesis of enantioenriched propargylic fluorides†

Laurence Carroll,^a Samantha McCullough,^a Tom Rees,^a Timothy D. W. Claridge^a and Véronique Gouverneur*^a

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* Corresponding authors

^a University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, UK
E-mail: veronique.gouverneur@chem.ox.ac.uk
Fax: +44 (0)1865 275 644

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 S_E2′ mechanism for the fluorination step.

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Supplementary files

Procedures for the preparation of all racemic and enantioenriched compounds are provided as well as full characterisation of all new compounds. PDF (339K)

Article information

DOI: https://doi.org/10.1039/B803888K
Article type: Communication
Submitted: 06 Mar 2008
Accepted: 20 Mar 2008
First published: 03 Apr 2008

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Org. Biomol. Chem., 2008,6, 1731-1733

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Stereospecific anti S_E2′ 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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Organic & Biomolecular Chemistry