Synthesis of the chiral diphosphine ligand 2, 3-bis (diphenylphosphino) butane (CHIRAPHOS)

U Matteoli, V Beghetto, C Schiavon, A Scrivanti…

Index: Matteoli, Ugo; Beghetto, Valentina; Schiavon, Cristina; Scrivanti, Alberto; Menchi, Gloria Tetrahedron Asymmetry, 1997 ,  vol. 8,  # 9  p. 1403 - 1409

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Citation Number: 22

Abstract

A new synthesis of CHIRAPHOS starting from readily available 2, 3-bis (diphenylphosphinyl)- 1, 3-butadiene has been devised. The key step of the synthesis is the hydrogenation of the diene to rac-2, 3-bis (diphenylphosphinyl) butane. This reduction can be conveniently performed by treating 2, 3-bis (diphenylphosphinyl)-1, 3-butadiene with NaBH4 in THF/CH2Cl2 mixtures. The racemic diphosphine oxides are subsequently resolved using ...