Tetrahedron: Asymmetry

Synthesis and resolution of 1-(2-diphenylphosphino-1-naphthyl) isoquinoline; a P N chelating ligand for asymmetric catalysis.

NW Alcock, JM Brown, DI Hulmes

Index: Alcock, Nathaniel W.; Brown, John M.; Hulmes, David I. Tetrahedron: Asymmetry, 1993 , vol. 4, # 4 p. 743 - 756

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Citation Number: 253

Abstract

Abstract A multistep synthesis resulting in a good yield of the title compound has been developed based on the Pd-catalysed coupling of 1-chloroisoquinoline and 2-methoxy-1- naphthylboronic acid (5). The product is converted into the corresponding trifluoromethanesulphonate (10) by successive demethylation and treatment with (CF 3 CO) 2 O, followed by a further Pd-catalysed coupling with Ph 2 P (O) H. The resulting ...