Lithium-Sulfoxide-Lithium exchange for the asymmetric synthesis of atropisomers under thermodynamic control

J Clayden, D Mitjans, LH Youssef

Index: Anstiss, Mark; Clayden, Jonathan; Grube, Alexander; Youssef, Latifa H. Synlett, 2002 , # 2 p. 290 - 294

Full Text: HTML

Citation Number: 94

Abstract

Ortholithiation and reaction with (-)-menthyl p-toluenesulfinate introduces a sulfoxide substituent ortho to the stereogenic Ar-CO axis of an aromatic amide. The sulfoxide exerts a powerful conformational bias on the axis, such that after rapid equilibration at ambient