Highly stereoselective hydroxy-directed Diels-Alder reaction

被引：40
作者：
Barriault, L [1 ]
Thomas, JDO [1 ]
Clément, R [1 ]
机构：
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 06期
关键词：
D O I：
10.1021/jo020664m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The successful stereocontrol of the Diels-Alder reaction of semicyclic dienes possessing a secondary and tertiary allylic magnesium alkoxide alcohol functionality and activated dienophiles such as methyl acrylate, methacrolein, acrolein, and N-phenylmaleimide is described.
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页码：2317 / 2323
页数：7
相关论文
共 53 条
[1]   Alkenylboronate tethered intramolecular Diels-Alder reactions [J].
Batey, RA ;
Thadani, AN ;
Lough, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :450-451
[2]   Temporary in situ aluminum and zinc tethering in Diels-Alder reactions [J].
Bertozzi, F ;
Olsson, R ;
Frejd, T .
ORGANIC LETTERS, 2000, 2 (09) :1283-1286
[3]   MODELING OF STERIC CONTROL OF FACIAL STEREOSELECTIVITY - DIELS-ALDER CYCLOADDITIONS OF UNSYMMETRICALLY SUBSTITUTED CYCLOPENTADIENES [J].
BROWN, FK ;
HOUK, KN ;
BURNELL, DJ ;
VALENTA, Z .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (14) :3050-3059
[4]   TORSIONAL AND STERIC CONTROL OF STEREOSELECTIVITY IN ISODICYCLOPENTADIENE CYCLO-ADDITIONS [J].
BROWN, FK ;
HOUK, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :1971-1978
[5]   PI-FACIAL STEREOSELECTIVITY IN THE DIELS-ALDER REACTIONS OF A RIGID CARBOCYCLIC DIENE - SPIRO(BICYCLO[2.2.1]HEPTANE-2,1'-[2,4]CYCLOPENTADIENE) [J].
BURNELL, DJ ;
VALENTA, Z .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1991, 69 (01) :179-184
[6]   Enantioselective Diels-Alder cycloadditions with (SS)-2-(p-tolylsulfinyl)-1,4-naphthoquinone:: Efficient kinetic resolution of chiral racemic vinylcyclohexenes [J].
Carreño, MC ;
Urbano, A ;
Di Vitta, C .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8320-8330
[7]  
Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO
[8]  
2-B
[9]   FIRST EXAMPLE OF A HIGHLY ENANTIOSELECTIVE CATALYTIC DIELS-ALDER REACTION OF AN ACHIRAL C-2-NU-SYMMETRICAL DIENOPHILE AND AN ACHIRAL DIENE [J].
COREY, EJ ;
SARSHAR, S ;
LEE, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12089-12090
[10]  
Coxon JM, 1999, SYNLETT, P1681
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