Synthesis of (E)-α,β-unsaturated esters with total diastereoselectivity by using chromium dichloride

被引：17

作者：

Concellón, JM ^{[1
]}

Rodríguez-Solla, H ^{[1
]}

Méjica, C ^{[1
]}

机构：

[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 14期

关键词：

chromium; eliminations; esters;

D O I：

10.1016/j.tetlet.2004.02.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of di- and trisubstituted (E)-alpha,beta-unsaturated esters is easily achieved by using chromium dichloride through an elimination reaction of a diastereoisomeric mixture of alpha-halo-beta-hydroxy esters. The starting materials were easily prepared by the aldol reaction of lithium enolates of alpha-chloroesters with aldehydes. A mechanism to explain this elimination process is proposed. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2977 / 2979

页数：3

共 44 条

[21] STEREOCHEMISTRY OF REDUCTIVE ELIMINATION BY CHROMIUM(2) COMPLEXES [J].

KOCHI, JK ;

SINGLETO.DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (06) :1582-&

[22] Development of a new Lewis acid-catalyzed [3,3]-sigmatropic rearrangement: The allenoate-claisen rearrangement [J].

Lambert, TH ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (46) :13646-13647

[23]

Liao B., 2000, HETEROCYCLES, V52, P1241

[24] Polylithiumorganic compounds. Part 27: C,C-bond forming reactions of 3,4-dilithio-2,5-dimethyl-2,4-hexadiene [J].

Maercker, A ;

van de Flierdt, J ;

Girreser, U .

TETRAHEDRON, 2000, 56 (21) :3373-3383

[25] THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS [J].

MARYANOFF, BE ;

REITZ, AB .

CHEMICAL REVIEWS, 1989, 89 (04) :863-927

[26] Stereospecific preparation of ethyl (E) and (Z)-3-aryl-3-phenylpropenoates by Heck reaction. [J].

MorenoManas, M ;

Perez, M ;

Pleixats, R .

TETRAHEDRON LETTERS, 1996, 37 (41) :7449-7452

[27] (E)-SELECTIVE OLEFINATION OF ALDEHYDES BY MEANS OF GEM-DICHROMIUM REAGENTS DERIVED BY REDUCTION OF GEM-DIIODOALKANES WITH CHROMIUM(II) CHLORIDE [J].

OKAZOE, T ;

TAKAI, K ;

UTIMOTO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :951-953

[28] A NEW VERSION OF THE PETERSON OLEFINATION USING BIS(TRIMETHYLSILYL)METHYL DERIVATIVES AND FLUORIDE-ION AS CATALYST [J].

PALOMO, C ;

AIZPURUA, JM ;

GARCIA, JM ;

GANBOA, I ;

COSSIO, FP ;

LECEA, B ;

LOPEZ, C .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2498-2503

[29]

PATAI S, 1968, CHEM ALKENES, P2

[30] Wittig reactions in the presence of silica gel [J].

Patil, VJ ;

Mavers, U .

TETRAHEDRON LETTERS, 1996, 37 (08) :1281-1284

← 1 2 3 4 5 →