Rhodium-catalysed asymmetric ring opening reactions with carboxylate nucleophiles

被引：77

作者：

Lautens, M ^{[1
]}

Fagnou, K ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

来源：

TETRAHEDRON | 2001年 / 57卷 / 24期

基金：

加拿大自然科学与工程研究理事会;

关键词：

asymmetric catalysis; rhodium; carboxylate;

D O I：

10.1016/S0040-4020(01)00351-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an asymmetric ring opening reaction of oxabenzonorbornadiene with carboxylate nucleophiles to generate enantiomerically enriched hydronaphthalene products containing an allylic carboxylate moiety. These reactions occur in good yield and excellent enantioselectivity (>90% ee). The allylic carboxylate functionality was found to be stable towards reaction with the rhodium catalyst under the reaction conditions. In order to obtain these results, two advancements were required. First, the use of protic additives was necessary for good reactivity. Second, the exchange of the halide Ligand on the catalyst from chloride to iodide was required to obtain high ee. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5067 / 5072

页数：6

共 45 条

[1] DIALKYLATION AND METHOXYALKYLATION OF BUTADIENE WITH DIETHYL MALONATE ANIONS [J].

AKERMARK, B ;

LJUNGQVIST, A ;

PANUNZIO, M .

TETRAHEDRON LETTERS, 1981, 22 (11) :1055-1058

[2] ASYMMETRIC-SYNTHESIS OF THE AB RING SEGMENTS OF DAUNOMYCIN AND 4-DEMETHOXYDAUNOMYCIN [J].

DAVIS, FA ;

CLARK, C ;

KUMAR, A ;

CHEN, BC .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) :1184-1190

[3]

DVORAK D, 1996, J AM CHEM SOC, V118, pW897

[4] Conservation of absolute configuration in the acyclic rhodium-catalyzed allylic alkylation reaction:: Evidence for an enyl (σ+π) organorhodium intermediate [J].

Evans, PA ;

Nelson, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5581-5582

[5] Regioselective and enantiospecific rhodium-catalyzed intermolecular allylic etherification with ortho-substituted phenols [J].

Evans, PA ;

Leahy, DK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) :5012-5013

[6] Enantiospecific synthesis of allylamines via the regioselective rhodium-catalyzed allylic amination reaction [J].

Evans, PA ;

Robinson, JE ;

Nelson, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6761-6762

[7] Rhodium-catalyzed ring opening of vinyl epoxides with alcohols and aromatic amines [J].

Fagnou, K ;

Lautens, M .

ORGANIC LETTERS, 2000, 2 (15) :2319-2321

[8] NAPHTHO AND BENZO ANALOGS OF THE KAPPA OPIOID AGONIST TRANS-(+/-)-3,4-DICHLORO-N-METHYL-N-[2-(1-PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE [J].

FREEMAN, JP ;

MICHALSON, ET ;

DANDREA, SV ;

BACZYNSKYJ, L ;

VONVOIGTLANDER, PF ;

LAHTI, RA ;

SMITH, MW ;

LAWSON, CF ;

SCAHILL, TA ;

MIZSAK, SA ;

SZMUSZKOVICZ, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (06) :1891-1896

[9] FACILE SYNTHESIS OF VINYLIC CYCLOPROPANES CARBOXYLATES WITH BIS [ETHYLENE BIS(DIPHENYLPHOSPHINE)] PALLADIUM (O) AS CATALYST [J].

GENET, JP ;

BALABANE, M ;

CHARBONNIER, F .

TETRAHEDRON LETTERS, 1982, 23 (48) :5027-5030

[10] A NOVEL SYNTHESIS OF (+/-)-TRANS-CHRYSANTHEMIC ACID [J].

GENET, JP ;

PIAU, F ;

FICINI, J .

TETRAHEDRON LETTERS, 1980, 21 (33) :3183-3186

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