Rhodium-catalyzed reaction of aryl and alkenylboronic acids with 2,4-dienoate esters:: Conjugate addition and Heck reaction products

被引：36

作者：

de la Herrán, G ^{[1
]}

Murcia, C ^{[1
]}

Csáky, AG ^{[1
]}

机构：

[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ, E-28040 Madrid, Spain

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 25期

关键词：

D O I：

10.1021/ol0522485

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We report herein the first examples of the addition of aryl- and alkenylboronic acids catalyzed by Rh-1 complexes to 2,4-dienoate esters. Three different types of products have been obtained depending on the substitution pattern of the starting ester and the organoboronic acid: 1,6-conjugate addition products, 1,4-conjugate addition products, and Heck reaction products.

引用

页码：5629 / 5632

页数：4

共 43 条

[21] NICKEL-CATALYZED SUBSTITUTION-REACTIONS OF ALLYLIC CARBONATES WITH ARYL-BORATES AND ALKENYL-BORATES [J].

KOBAYASHI, Y ;

IKEDA, E .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (15) :1789-1790

[22]

Kozlowski J. A, 1991, COMPREHENSIVE ORGANI, V4, P169

[23] Copper-mediated 1,6-, 1,8-, 1,10-and 1,12-addition and 1,5-substitution reactions in organic synthesis [J].

Krause, N ;

Thorand, S .

INORGANICA CHIMICA ACTA, 1999, 296 (01) :1-11

[24] 1,6-ADDITION AND 1,8-ADDITION REACTIONS OF ORGANOCUPRATES TO MICHAEL ACCEPTORS - NMR-SPECTROSCOPIC OBSERVATION OF THE INTERMEDIATES AND CONCLUSIONS ABOUT THE REACTION-MECHANISM [J].

KRAUSE, N .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3509-3512

[25]

Krause N, 2001, SYNTHESIS-STUTTGART, P171

[26]

LISHUTZ BH, 2002, ORGANOMETALLICS ORGA, P665

[27] STEREOCHEMICAL STUDIES ON 1,6 ADDITIONS TO 10-METHYL-I(9),7-HEXAL-2-ONE BY GRIGNARD REAGENTS [J].

MARSHALL, JA ;

ROEBKE, H .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (10) :3109-&

[28]

MARSHALL JA, 1971, TETRAHEDRON LETT, P3795

[29] PALLADIUM-CATALYZED CROSS-COUPLING OF ALLYLIC CARBONATES WITH ALKENYLFLUOROSILANES IN THE ABSENCE OF FLUORIDE-ION [J].

MATSUHASHI, H ;

HATANAKA, Y ;

KUROBOSHI, M ;

HIYAMA, T .

TETRAHEDRON LETTERS, 1995, 36 (09) :1539-1540

[30] Novel (2E,4E,6Z)-7-(2-alkoxy-3,5-dialkylbenzene)-3-methylocta-2,4,6-trienoic acid retinoid X receptor modulators are active in models of type 2 diabetes [J].

Michellys, PY ;

Ardecky, RJ ;

Chen, JH ;

Crombie, DL ;

Etgen, GJ ;

Faul, MM ;

Faulkner, AL ;

Grese, TA ;

Heyman, RA ;

Karanewsky, DS ;

Klausing, K ;

Leibowitz, MD ;

Liu, S ;

Mais, DA ;

Mapes, CM ;

Marschke, KB ;

Reifel-Miller, A ;

Ogilvie, KM ;

Rungta, D ;

Thompson, AW ;

Tyhonas, JS ;

Boehm, MF .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (13) :2683-2696

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