Stereochemistry in palladium- and nickel-catalyzed addition of phenylmagnesium bromide to unsaturated carbohydrates

被引：7

作者：

Moineau, C ^{[1
]}

Bolitt, V ^{[1
]}

Sinou, D ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, Lab Synth Asymetr, CPE Lyon, F-69622 Villeurbanne, France

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1998年 / 567卷 / 1-2期

关键词：

palladium; nickel; Grignard reagents; arylation; stereochemistry; 2,3-unsaturated glycosides;

D O I：

10.1016/S0022-328X(98)00679-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Palladium complex PdCl2(dppf) and nickel complex NiCl2(dppe) catalyze cross-coupling of unsaturated aryloxy carbohydrates with phenylmagnesium bromide. The nickel catalyst leads to inversion of configuration at the anomeric center while only retention occurs in the case of the palladium catalyst. This quite unusal retention is probably due to the influence of the ring oxygen atom (C) 1998 Elsevier Science S.A. All rights reserved.

引用

页码：157 / 162

页数：6

共 29 条

[1]

[Anonymous], 1991, COMPREHENSIVE ORGANI

[2] STEREOCHEMICAL ASPECTS OF THE NICKEL-CATALYZED ALKYLATION OF ALLYLIC ALCOHOLS [J].

CONSIGLIO, G ;

MORANDINI, F ;

PICCOLO, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (07) :1846-1847

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

CONSIGLIO, G ;

WAYMOUTH, RM .

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

[4] DIRECTED REGIOSELECTIVE AND STEREOSELECTIVE NICKEL-CATALYZED ADDITION OF ALKYL GRIGNARD-REAGENTS TO ALLYLIC ETHERS [J].

DIDIUK, MT ;

MORKEN, JP ;

HOVEYDA, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) :7273-7274

[5] PALLADIUM-ASSISTED C-GLYCOSYLATION - ADDITION OF CARBANIONS TO CYCLIC ENOL ETHERS [J].

DUNKERTON, LV ;

SERINO, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (14) :2812-2814

[6] NEW METHOD FOR THE CLASSIFICATION OF NUCLEOPHILES IN THE PALLADIUM-CATALYZED SUBSTITUTION OF ALLYLIC ACETATES [J].

FIAUD, JC ;

LEGROS, JY .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) :1907-1911

[7] PALLADIUM-CATALYZED ASYMMETRIC COUPLING REACTIONS BETWEEN ALLYLIC ACETATES AND ORGANOZINC REAGENTS - MECHANISTIC IMPLICATIONS [J].

FIAUD, JC ;

ARIBIZOUIOUECHE, L .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 295 (03) :383-387

[8] CARBON CARBON BOND FORMATION BY INDUCED ELIMINATION FROM UNSYMMETRICALLY SUBSTITUTED (ALLYL)(ALLYL') PALLADIUM COMPLEXES [J].

GOLIASZEWSKI, A ;

SCHWARTZ, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) :5028-5030

[9] REGIO-CHEMISTRY AND STEREO-CHEMISTRY IN ALLYLATION OF ARYL GRIGNARD-REAGENTS CATALYZED BY PHOSPHINE-NICKEL AND PHOSPHINE-PALLADIUM COMPLEXES [J].

HAYASHI, T ;

KONISHI, M ;

YOKOTA, KI ;

KUMADA, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :359-373

[10] DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM-(II) - AN EFFECTIVE CATALYST FOR CROSS-COUPLING OF SECONDARY AND PRIMARY ALKYL GRIGNARD AND ALKYLZINC REAGENTS WITH ORGANIC HALIDES [J].

HAYASHI, T ;

KONISHI, M ;

KOBORI, Y ;

KUMADA, M ;

HIGUCHI, T ;

HIROTSU, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (01) :158-163

← 1 2 3 →