Tetrahedron

Sulfoxides as 'traceless' resolving agents for the synthesis of atropisomers by dynamic or classical resolution

J Clayden, PM Kubinski, F Sammiceli, M Helliwell…

Index: Clayden, Jonathan; Kubinski, Przemyslaw M.; Sammiceli, Federica; Helliwell, Madeleine; Diorazio, Louis Tetrahedron, 2004 , vol. 60, # 20 p. 4387 - 4397

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Citation Number: 40

Abstract

Reacting (−)-menthyl sulfinate with an atropisomeric but racemic aryllithium gives two atropdiastereoisomeric sulfoxides. Separation (by chromatography or crystallisation) and sulfoxide–lithium exchange of each diastereoisomer regenerates the aryllithium in enantiomerically pure form which can be quenched with a range of electrophiles with retention of stereochemical integrity. Overall the reaction sequence is a resolution but ...