Radical addition to vinylphosphine oxides: 1, 2-stereoinduction of phosphorus stercogcnic centre

A Brandi, S Cicchi, A Goti, KM Pietrusiewiez

Index: Brandi, Alberto; Cicchi, Stefano; Goti, Andrea; Pietrusiewiez, K. Michal Tetrahedron Letters, 1991 , vol. 32, # 27 p. 3265 - 3268

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Citation Number: 17

Abstract

Abstract Carbon cantered radicals derived from reactions of halides 3–5 with Bu 3 SnH in the presence of AIBN havebeentrapped by diphenylvinylphosphine oxide 2 giving the addition products 6–8 in high yields. Free radical addition to 2 employing the Barton methodology gave lower yields. The use of chiral (racemic:) vinylphosphine oxides allowed a stereoselective radical addition with a diastercomeric ratio as high as 9: 1 for ...