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Bu4N+ Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes

Manas Das and Donal F. O’Shea*

*Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen’s Green, Dublin 2, Ireland, Email: donalfoshearcsi.ie

M. Das, D. F. O'Shea, J. Org. Chem., 2014, 79, 5595-5607.

DOI: 10.1021/jo5007637 (free Supporting Information)


Abstract

The combination of Me3SiO- and Bu4N+ serves as a general activator of organotrimethylsilanes for addition reactions. A broad scope of bench-stable trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) can be used as carbanion equivalents for synthesis. Reactions are achieved at rt without the requirement of specialized precautions that are commonplace for other organometallics.

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Key Words

1,2-addition, benzylic alcohols, homoallylic alcohols


ID: J42-Y2014