Carbon centered radicals derived from reactions of halides 3-5 with Bu3SnH in the presence of AIBN have been trapped 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 diastereomeric ratio as high as 9:1 for mesitylmethylvinylphosphine oxide 1.

Radical Addition to Vinylphosphine Oxides: 1,2-Stereoinduction of Phosphorous Stereogenic Centre / A. BRANDI; S. CICCHI; A. GOTI; K. M. PIETRUSIEWICZ. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 32(1991), pp. 3265-3268. [10.1016/S0040-4039(00)79740-1]

Radical Addition to Vinylphosphine Oxides: 1,2-Stereoinduction of Phosphorous Stereogenic Centre

BRANDI, ALBERTO;CICCHI, STEFANO;GOTI, ANDREA;
1991

Abstract

Carbon centered radicals derived from reactions of halides 3-5 with Bu3SnH in the presence of AIBN have been trapped 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 diastereomeric ratio as high as 9:1 for mesitylmethylvinylphosphine oxide 1.
32
3265
3268
A. BRANDI; S. CICCHI; A. GOTI; K. M. PIETRUSIEWICZ
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/7320
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