THE 1ST SYNTHESIS OF CHIRAL PHOSPHINOCARBOXYLIC ACID LIGANDS, TRANS-2-(DIPHENYLPHOSPHINO)CYCLOALKANECARBOXYLIC ACIDS - THE PHOSPHINE-PALLADIUM COMPLEXES CATALYZED ASYMMETRIC ALLYLIC ALKYLATION

被引：33

作者：

OKADA, Y ^{[1
]}

MINAMI, T ^{[1
]}

SASAKI, Y ^{[1
]}

UMEZU, Y ^{[1
]}

YAMAGUCHI, M ^{[1
]}

机构：

[1] KYUSHU INST TECHNOL,DEPT APPL CHEM,KITAKYUSHU 804,JAPAN

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(00)97502-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesized chiral phosphinocarboxylic acids were effective as ligand for the palledium-catalyzed asymmetric allylic alkylation of 3-acetoxy-1,3-diphenyl-1-propene and 2-cyclohexenyl acetate with soft carbanion from dimethyl malonate or triethyl phosphonoacetate and sodium hydride to give the alkylation products of up to 83% ee. © 1990.

引用

页码：3905 / 3908

页数：4

共 16 条

[1] ASYMMETRIC-SYNTHESIS - ASYMMETRIC CATALYTIC ALLYLATION USING PALLADIUM CHIRAL PHOSPHINE COMPLEXES [J].

AUBURN, PR ;

MACKENZIE, PB ;

BOSNICH, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2033-2046

[2] ENANTIOSELECTIVE HOMOGENEOUS CATALYSIS INVOLVING TRANSITION-METAL ALLYL INTERMEDIATES [J].

CONSIGLIO, G ;

WAYMOUTH, RM .

CHEMICAL REVIEWS, 1989, 89 (01) :257-276

[3] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .8. PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC AMINATION [J].

HAYASHI, T ;

YAMAMOTO, A ;

ITO, Y ;

NISHIOKA, E ;

MIURA, H ;

YANAGI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6301-6311

[4] 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

[5] ASYMMETRIC CATALYTIC HYDROGENATION WITH AN OPTICALLY ACTIVE PHOSPHINERHODIUM COMPLEX IN HOMOGENEOUS SOLUTION [J].

HORNER, L ;

SIEGEL, H ;

BUTHE, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (12) :942-&

[6] ASYMMETRIC CATALYTIC REDUCTION WITH TRANSITION-METAL COMPLEXES .1. CATALYTIC SYSTEM OF RHODIUM(I) WITH (-)-2,3-O-ISOPROPYLIDENE-2,3-DIHYDROXY-1,4-BIS(DIPHENYLPHOSPHINO)BUTANE - NEW CHIRAL DIPHOSPHINE [J].

KAGAN, HB ;

DANG, TP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (18) :6429-&

[7]

Knowles W.S., 1968, J CHEM SOC CHEM COMM, P1445, DOI DOI 10.1039/C19680001445

[8] STEREOSPECIFIC SYNTHESIS OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES OF TRANS-1,3-DIHYDROXYCYCLOALKANES [J].

MARINO, JP ;

FARINA, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (19) :3213-3215

[9]

Mason R. F., 1972, US Pat, Patent No. [3 686 351, 3686351]

[10] SYNTHESIS AND REACTIONS OF THE (1-CYCLOBUTENYL)TRIPHENYLPHOSPHONIUM SALT [J].

MINAMI, T ;

SAKO, H ;

IKEHIRA, T ;

HANAMOTO, T ;

HIRAO, I .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (15) :2569-2572

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