Article ID Journal Published Year Pages File Type
5223587 Tetrahedron 2008 8 Pages PDF
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 2 to 1) were obtained.

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Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry