Planar tether control groups and pi-facial selectivity: Intramolecular cycloadditions for polycyclic systems

被引：14

作者：

Millan, DS ^{[1
]}

Pham, TT ^{[1
]}

Lavers, JA ^{[1
]}

Fallis, AG ^{[1
]}

机构：

[1] UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA,ON K1N 6N5,CANADA

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 05期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(96)02459-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct synthesis of the fused ring systems II (R = Me, H) and the decalin 14 are described. The use of a planar. tether control group (either aromatic ring or double bond) greatly facilitates the key Diels-Alder cycloadditions. A second intermolecular cycloaddition of 14 with cyclopentadiene afforded the tetracyclic adduct 17. The interaction between the allylic ethers and diene substituents influences the facial selectivity observed in these examples. (C) 1997, Elsevier Science Ltd.

引用

页码：795 / 798

页数：4

共 23 条

[1] [Anonymous], 1991, Comprehensive Organic Synthesis
[2] [Anonymous], 1991, Comprehensive Organic Synthesis
[3] ACYL RADICALS - FUNCTIONALIZED FREE-RADICALS FOR INTRAMOLECULAR CYCLIZATION REACTIONS
BOGER, DL
MATHVINK, RJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) : 3377 - 3379
[4] BOYES DL, 1991, COMPREHENSIVE ORGANI, V5, P451
[5] Carruthers W, 1990, Cycloaddition Reactions in Organic Synthesis
[6] Ciganek E., 1984, ORG REACT NY, V32, P1, DOI DOI 10.1002/0471264180.OR032.01
[7] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION
CRAIG, D
[J]. CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) : 187 - 238
[8] A SIMPLE AND DIRECT METHOD OF CYCLIZATION FOR THE SYNTHESIS OF 10-MEMBERED RINGS
DESLONGCHAMPS, P
LAMOTHE, S
LIN, HS
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (06): : 1298 - 1307
[9] Formation of macrocycles by catalytic intramolecular aromatic cycloaddition of metal carbenes to remote arenes
Doyle, MP
Protopopova, MN
Peterson, CS
Vitale, JP
McKervey, MA
Garcia, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (33) : 7865 - 7866
[10] THE INTRAMOLECULAR DIELS-ALDER REACTION - RECENT ADVANCES AND SYNTHETIC APPLICATIONS
FALLIS, AG
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (02): : 183 - 234

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