SYNTHESIS OF THE CHIRAL DIPHOSPHINE LIGAND 2,3-BIS(DIPHENYLPHOSPHINO)BUTANE (CHIRAPHOS)

Authors
MATTEOLI U BEGHETTO V SCHIAVON C SCRIVANTI A MENCHI G
Citation
U. Matteoli et al., SYNTHESIS OF THE CHIRAL DIPHOSPHINE LIGAND 2,3-BIS(DIPHENYLPHOSPHINO)BUTANE (CHIRAPHOS), Tetrahedron : asymmetry, 8(9), 1997, pp. 1403-1409
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
9
Year of publication
1997
Pages
1403 - 1409
Database
ISI
SICI code
0957-4166(1997)8:9<1403:SOTCDL>2.0.ZU;2-I
Abstract
A new synthesis of CHIRAPHOS starting from readily available 2,3-bis(d iphenylphosphinyl)-1,3-butadiene has been devised. The key step of the synthesis is the hydrogenation of the diene to rac-2,3-bis(diphenylph osphinyl)butane. This reduction can be conveniently performed by treat ing 2,3-bis(diphenylphosphinyl)-1,3-butadiene with NaBH4 in THF/CH2Cl2 mixtures. The racemic diphosphine oxides are subsequently resolved us ing (2S,3S)-(+)- and (2R,3R)-(-)-2,3-O-dibenzoyltartaric acid [(+)- an d (-)-DBTA]. Reduction of the resolved phosphine oxides is carried out using trichlorosilane. (C) 1997 Elsevier Science Ltd.