Tetrahedron

Atroposelective radical aryl migration reactions from sulfur to carbon

B Schulte, R Fröhlich, A Studer

Index: Schulte, Birte; Froehlich, Roland; Studer, Armido Tetrahedron, 2008 , vol. 64, # 52 p. 11852 - 11859

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Citation Number: 12

Abstract

The paper describes stereoselective radical aryl migration reactions from sulfur in sulfonates to aryl radicals for the synthesis of axially chiral biaryls. A chirality center in secondary benzylic sulfonates is used to diastereoselectively (atroposelectively) install a stereogenic axis via a 1, 5 aryl migration reaction. Atroposelectivity has not been investigated in stereoselective radical chemistry before. Good yields (53–82%) but low selectivities (up to ...