Intramolecular 1,3-dipolar cycloadditions of norbornadiene-tethered nitrile oxides

被引：37

作者：

Yip, C ^{[1
]}

Handerson, S ^{[1
]}

Tranmer, GK ^{[1
]}

Tam, W ^{[1
]}

机构：

[1] Univ Guelph, Guelph Waterloo Ctr Grad Work Chem, Dept Chem & Biochem, Guelph, ON N1G 2W1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 01期

关键词：

D O I：

10.1021/jo005611o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient routes to the synthesis of norbornadiene-tethered nitrile oxide; have been developed, and their intramolecular 1.3-dipolar cycloadditions were studied. The cycloadditions occurred in good yields for a variety of substrates and were found to be highly regio- and stereoselective, giving single regio- and stereoisomers in most cases.

引用

页码：276 / 286

页数：11

共 50 条

[31] 1,3-Dipolar cycloadditions of nitrile oxides with 7-oxa- and 7-azabenzonorbornadienes
Nagireddy, Jaipal R.
Carlson, Emily
Tam, William
CANADIAN JOURNAL OF CHEMISTRY, 2014, 92 (07) : 635 - 639
[32] REGIOCHEMICAL CONSEQUENCES OF C-HAL HYPERCONJUGATION IN 1,3-DIPOLAR CYCLOADDITIONS OF NITRILE OXIDES
BELTRAME, P
BELTRAME, PL
CARAMELLA, P
CELLERINO, G
FANTECHI, R
TETRAHEDRON LETTERS, 1975, (41) : 3543 - 3546
[33] Synthesis of functionalized benzopyrans via intramolecular 1,3-dipolar cycloaddition of nitrile oxides
Vaidya, Vipraja V.
Wankhede, Karuna S.
Salunkhe, Manikrao M.
Trivedi, Girish K.
SYNTHETIC COMMUNICATIONS, 2008, 38 (14) : 2392 - 2403
[34] Transition structures of diastereoselective 1,3-dipolar cycloadditions of nitrile oxides to chiral homoallylic alcohols
Luft, Jennifer A. R.
Meleson, Kieche
Houk, K. N.
ORGANIC LETTERS, 2007, 9 (04) : 555 - 558
[35] 1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with nitrile oxides and nitrones
Kissane, Marie
Lawrence, Simon E.
Maguire, Anita R.
TETRAHEDRON, 2010, 66 (25) : 4564 - 4572
[36] 1,3-DIPOLAR CYCLOADDITIONS OF 1,1-DIFLUOROALLENE, NITRONES, NITRILE OXIDES AND CARBONYL YLIDES
DOLBIER, WR
BURKHOLDER, CR
ISRAEL JOURNAL OF CHEMISTRY, 1985, 26 (02) : 115 - 119
[37] 1,3-dipolar cycloadditions in the synthesis of carbohydrate mimics. Part 1: Nitrile oxides and nitronates
Gallos, JK
Koumbis, AE
CURRENT ORGANIC CHEMISTRY, 2003, 7 (05) : 397 - 425
[38] 1,3-DIPOLAR CYCLOADDITIONS TO BICYCLIC OLEFINS .3. EFFECTS OF AROMATIC SOLVENTS ON EXO-ENDO PRODUCT RATIOS FOR 1,3-DIPOLAR CYCLOADDITIONS OF NITRILE OXIDES TO NORBORNADIENES
TANIGUCHI, H
IMOTO, E
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (08) : 2405 - 2409
[39] 1,3-DIPOLAR CYCLOADDITIONS WITH DIAZOMETHYLPHOSPHONATES - DOUBLE PYRAZOLINES DERIVED FROM NORBORNADIENE
COHEN, H
BENEZRA, C
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (01): : 44 - 52
[40] Catalytic, enantioselective 1,3-dipolar cycloadditions of nitrile imines with methyleneindolinones
Gerten, Anthony L.
Slade, Michael C.
Pugh, Kelsie M.
Stanley, Levi M.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (45) : 7834 - 7837

← 1 2 3 4 5 →