Asymmetric synthesis of an axially chiral antimitotic biaryl via an atropo-enantioselective Suzuki cross-coupling

A Herrbach, A Marinetti, O Baudoin…

Index: Herrbach, Audrey; Marinetti, Angela; Baudoin, Olivier; Guenard, Daniel; Gueritte, Francoise Journal of Organic Chemistry, 2003 , vol. 68, # 12 p. 4897 - 4905

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Citation Number: 107

Abstract

A catalytic asymmetric synthesis of the axially chiral bridged biaryl (-)-2, a structural analogue of natural (-)-rhazinilam possessing original antimitotic properties, is described. The key step is an intermolecular asymmetric Suzuki coupling, furnishing the nonbridged biaryl (-)-6, precursor of (-)-2, with up to 40% ee using binaphthyl ligand 7a. Various known or new binaphthyl and ferrocenyl phosphines as well as phosphetanes were screened as ...

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