A New and Selective α′-Bromination of α,β-Unsaturated Ketones

M. J. S. Miranda Moreno; M. L. Sá e Melo; A. S. Campos Neves

doi:10.1055/s-1994-22962

Synlett 1994; 1994(8): 651-652
DOI: 10.1055/s-1994-22962

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A New and Selective α′-Bromination of α,β-Unsaturated Ketones

M. J. S. Miranda Moreno^* , M. L. Sá e Melo, A. S. Campos Neves

^*Laboratório de Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, 3000 Coimbra, PORTUGAL

Abstract

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α′-Bromination of α,β-unsaturated ketones was carried out via trialkylsilyl dienol ethers with phenyltrimethylammonium tribromide. This reagent, which has not been previously used to brominate such derivatives, allows a high degree of selectivity under mild reaction conditions with the further advantage of not requiring the isolation of the silyl intermediates. The bromination selectivity is dependent on the trialkylsilyl group present on the dienol ether.

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