Cationic Rh(I) catalyst in fluorinated alcohol: Mild intramolecular cycloaddition reactions of ester-tethered unsaturated compounds

被引：45

作者：

Saito, Akio ^{[1
]}

Ono, Takamitsu ^{[1
]}

Hanzawa, Yuji ^{[1
]}

机构：

[1] Showa Pharmaceut Univ, Lab Organ React Chem, Machida, Tokyo 1948543, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 17期

关键词：

DIELS-ALDER REACTIONS; ENANTIOSELECTIVE SYNTHESES; DECALINIC STRUCTURES; INTERMOLECULAR 5+2; FORMAL SYNTHESIS; STEREOCONTROL; 1,7,9-DECATRIENOATES; ALKYNES;

D O I：

10.1021/jo060827x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In fluorinated alcohols, the cationic Rh(I) species, which is derived from [Rh(COD) Cl](2) and AgSbF6, efficiently catalyzed intramolecular [4+2] cycloaddition reactions of ester-tethered 1,3-diene-8-yne derivatives. The catalytic system was also effective in intramolecular [5+2] cycloaddition reactions of ester-tethered omega-alkynyl vinylcyclopropane compounds.

引用

页码：6437 / 6443

页数：7

共 55 条

[1] BIRTWHISTLE DH, 1998, TETRAHEDRON, V44, P7309
[2] STEREOCONTROL IN THE INTRAMOLECULAR DIELS-ALDER REACTION .4. A REMARKABLE EFFECT OF OVERLAP REQUIREMENTS IN THE CONNECTING CHAIN
BOECKMAN, RK
DEMKO, DM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (09) : 1789 - 1792
[3] Barriers to rotation in methyl formate by dynamic NMR spectroscopy and barriers to 1,3 oxygen-to-oxygen migration in methyl formate and trifluoromethyl formate by ab initio calculations
Cain, D
Pawar, DM
Stewart, M
Billings, H
Noe, EA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (18) : 6092 - 6095
[4] Rh-catalyzed enyne cycloisomerization
Cao, P
Wang, B
Zhang, XM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) : 6490 - 6491
[5] Intramolecular Diels-Alder reactions of ester-linked 1,3,8-nonatrienes
Cayzer, TN
Paddon-Row, MN
Moran, D
Payne, AD
Sherburn, MS
Turner, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14) : 5561 - 5570
[6] Cayzer TN, 2002, CHEM-EUR J, V8, P739, DOI 10.1002/1521-3765(20020201)8:3<739::AID-CHEM739>3.0.CO
[7] 2-1
[8] Ciganek E., 1984, ORG REACT, V32, P1
[9] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION
CRAIG, D
[J]. CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) : 187 - 238
[10] DESLONGCHAMPS P, 1983, STEREOELECTRONIC EFF, P54

← 1 2 3 4 5 6 →