DEVELOPMENT OF CHIRAL PHOSPHINE-LIGANDS BEARING A CARBOXYL GROUP AND THEIR APPLICATION TO CATALYTIC ASYMMETRIC REACTION

被引：33

作者：

MINAMI, T ^{[1
]}

OKADA, Y ^{[1
]}

OTAGURO, T ^{[1
]}

TAWARAYA, S ^{[1
]}

FURUICHI, T ^{[1
]}

OKAUCHI, T ^{[1
]}

机构：

[1] KINKI UNIV,DEPT APPL CHEM,HIGASHIHIROSHIMA,HIROSHIMA 72917,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 10期

关键词：

D O I：

10.1016/0957-4166(95)00322-G

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new chiral phosphine ligand bearing a carboxyl group, 3-(diphenylphosphino)butanoic acid, was developed and used for palladium catalyzed asymmetric allylic alkylation of cyclic cis-allylic acetates such as 2-cyclopentenyl, 2-cyclohexenyl, and 2-cycloheptenyl acetate. These acetates reacted with triethyl sodiophosphonoacetate in the presence of the palladium catalyst with the ligand to give the corresponding alkylation products in good enantiomeric excesses.

引用

页码：2469 / 2474

页数：6

共 23 条

[1] INFLUENCE OF POSTURAL CHANGES ON GLOMERULAR-FILTRATION RATE IN NEPHROPTOSIS [J].

BIANCHI, C ;

BONADIO, M ;

ANDRIOLE, VT .

NEPHRON, 1976, 16 (03) :161-172

[2] A NEW CLASS OF CHIRAL PHOSPHORUS CATALYST FOR ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS [J].

BRENCHLEY, G ;

MERIFIELD, E ;

WILLS, M ;

FEDOULOFF, M .

TETRAHEDRON LETTERS, 1994, 35 (17) :2791-2794

[3] MECHANISTIC AND SYNTHETIC STUDIES IN CATALYTIC ALLYLIC ALKYLATION WITH PALLADIUM COMPLEXES OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE [J].

BROWN, JM ;

HULMES, DI ;

GUIRY, PJ .

TETRAHEDRON, 1994, 50 (15) :4493-4506

[4] PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS OF PROCHIRAL AND RACEMIC ALLYL ACETATES [J].

DAWSON, GJ ;

WILLIAMS, JMJ ;

COOTE, SJ .

TETRAHEDRON LETTERS, 1995, 36 (03) :461-462

[5] HOMOGENEOUS AND HETEROGENEOUS PD-CATALYZED ENANTIOSELECTIVE ALKYLATION WITH C-2-SYMMETRICAL CHIRAL NITROGEN LIGANDS [J].

GAMEZ, P ;

DUNJIC, B ;

FACHE, F ;

LEMAIRE, M .

TETRAHEDRON-ASYMMETRY, 1995, 6 (05) :1109-1116

[6] MODIFICATION OF OPTICALLY-ACTIVE FERROCENYLPHOSPHINE LIGANDS FOR PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC ALKYLATION [J].

HAYASHI, T ;

YAMAMOTO, A ;

HAGIHARA, T ;

ITO, Y .

TETRAHEDRON LETTERS, 1986, 27 (02) :191-194

[7] STEREOCHEMISTRY OF OXIDATIVE ADDITION OF AN OPTICALLY-ACTIVE ALLYL ACETATE TO A PALLADIUM(0) COMPLEX [J].

HAYASHI, T ;

HAGIHARA, T ;

KONISHI, M ;

KUMADA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) :7767-7768

[8]

HEUMANN A, 1993, ORG SYNTH COLL, V8, P137

[9] ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC ALKYLATION WITH PHOSPHORUS-CONTAINING C-2-SYMMETRICAL CHIRAL AMINE LIGANDS [J].

KUBOTA, H ;

KOGA, K .

TETRAHEDRON LETTERS, 1994, 35 (36) :6689-6692

[10] CONVENIENT METHOD FOR SYNTHESIS OF CARBOXYLIC ESTERS [J].

MUKAIYAMA, T ;

USUI, M ;

SHIMADA, E ;

SAIGO, K .

CHEMISTRY LETTERS, 1975, (10) :1045-1048

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