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

被引：19

作者：

Matteoli, U ^{[1
]}

Beghetto, V ^{[1
]}

Schiavon, C ^{[1
]}

Scrivanti, A ^{[1
]}

Menchi, G ^{[1
]}

机构：

[1] UNIV FLORENCE,DIPARTIMENTO CHIM ORGAN,I-50121 FLORENCE,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(97)00132-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

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 (2S,3S)-(+)- and (2R,3R)-(-)-2,3-O-dibenzoyltartaric acid [(+)- and (-)-DBTA]. Reduction of the resolved phosphine oxides is carried out using trichlorosilane. (C) 1997 Elsevier Science Ltd.

引用

页码：1403 / 1409

页数：7

共 10 条

[1] THE ASYMMETRIC HYDROFORMYLATION IN THE SYNTHESIS OF PHARMACEUTICALS
BOTTEGHI, C
PAGANELLI, S
SCHIONATO, A
MARCHETTI, M
[J]. CHIRALITY, 1991, 3 (04) : 355 - 369
[2] ASYMMETRIC SYNTHESIS - PRODUCTION OF OPTICALLY-ACTIVE AMINO-ACIDS BY CATALYTIC-HYDROGENATION
FRYZUK, MD
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (19) : 6262 - 6267
[3] HORNER L, 1965, TETRAHEDRON LETT, P1157
[4] MICHAEL ADDITION OF LITHIODIPHENYLPHOSPHINE TO MENTHYLOXY-2[5H]-FURANONE - ENANTIOSELECTIVE SYNTHESIS OF S,S-CHIRAPHOS
JANSEN, JFGA
FERINGA, BL
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (10) : 719 - 720
[5] MANDER LN, 1994, STEREOCHEMISTRY ORGA, pCH12
[6] Perrin D. D., 1988, PURIFICATION LAB CHE
[7] 2,3-BIS(DIPHENYLPHOSPHINYL)-1,3-BUTADIENE VIA A DOUBLE [2,3]-SIGMATROPIC REARRANGEMENT - A REINVESTIGATION OF THE REACTION OF 2-BUTYNE-1,4-DIOL WITH CHLORODIPHENYLPHOSPHINE
POLLOK, T
SCHMIDBAUR, H
[J]. TETRAHEDRON LETTERS, 1987, 28 (10) : 1085 - 1088
[8] SPENCER A, 1987, COMPREHENSIVE COORDI, V6, P250
[9] PRACTICAL SYNTHESIS OF (R)-2,2' OR (S)-2,2'-BIS(DIARYLPHOSPHINO)-1,1'-BINAPHTHYLS (BINAPS)
TAKAYA, H
MASHIMA, K
KOYANO, K
YAGI, M
KUMOBAYASHI, H
TAKETOMI, T
AKUTAGAWA, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) : 629 - 635
[10] TAKAYA H, 1988, ORG SYNTH, V67, P20

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