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Copper(I)-Catalyzed Regioselective Propargylic Substitution Involving Si-B Bond Activation

Devendra J. Vyas, Chinmoy K. Hazra and Martin Oestreich*

*Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany, Email: martin.oestreichtu-berlin.de

D. J. Vyas, C. K. Hazra, M. Oestreich, Org. Lett., 2011, 13, 4462-4465.

DOI: 10.1021/ol201811d (free Supporting Information)


Abstract

The silicon nucleophile generated by copper(I)-catalyzed Si-B bond activation allows several γ-selective propargylic substitutions. Chloride as a leaving groups is superior in linear substrates, and the phosphate group produces superb γ-selectivity in α-branched propargylic systems, and enantioenriched substrates react with excellent central-to-axial chirality transfer.


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Key Words

Allenes, Silanes


ID: J54-Y2011-2370