CYCLOADDITION REACTIONS OF 3,4-DIHYDRO-2H-PYRROLE 1-OXIDE WITH ALPHA,BETA-UNSATURATED LACTONES

被引：34

作者：

ALONSOPERARNAU, D ^{[1
]}

DEMARCH, P ^{[1
]}

FIGUEREDO, M ^{[1
]}

FONT, J ^{[1
]}

SORIA, A ^{[1
]}

机构：

[1] UNIV AUTONOMA BARCELONA,DEPT QUIM,E-08193 BARCELONA,SPAIN

来源：

TETRAHEDRON | 1993年 / 49卷 / 20期

关键词：

D O I：

10.1016/S0040-4020(01)85742-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cycloadditions of nitrone 2 to alpha,beta-unsaturated lactones 3-46 have been studied under several reaction conditions. The adducts derived from pentenolide 5 and hexenolide 6 are the first examples of the pyrano[3,4-d]pyrrolo[1,2-b]isoxazole and oxepino[3,4-d]pyrrolo[1,2-b]isoxazole systems respectively. The stereochemistry of the products has been established using high field nmr techniques. In all cases the major cycloadduct derives from an exo orientation of the transition state.

引用

页码：4267 / 4274

页数：8

共 36 条

[1] ALI SA, 1992, J CHEM RES, P146
[2] THE 1,3-DIPOLAR CYCLO-ADDITION OF CYCLIC NITRONES WITH 1,2-DISUBSTITUTED ALKENES
ALI, SA
KHAN, JH
WAZEER, MIM
PERZANOWSKI, HP
[J]. TETRAHEDRON, 1989, 45 (18) : 5979 - 5986
[3] ALI SA, 1990, TETRAHEDRON, V46, P7207
[4] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS
ALLINGER, NL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) : 8127 - 8134
[5] ANNUNZIATA R, 1989, GAZZ CHIM ITAL, V119, P253
[6] THE DIASTEREOSELECTIVITY OF INTERMOLECULAR NITRONE CYCLOADDITION TO CHIRAL ALLYL DERIVATIVES
ANNUNZIATA, R
CINQUINI, M
COZZI, F
GIARONI, P
RAIMONDI, L
[J]. TETRAHEDRON LETTERS, 1991, 32 (13) : 1659 - 1662
[7] REGIO-SELECTIVE AND FACE-SELECTIVE 1,3-DIPOLAR CYCLO-ADDITIONS TO LEVOGLUCOSENONE
BLAKE, AJ
FORSYTH, AC
PATON, RM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (06) : 440 - 442
[8] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF LEVOGLUCOSENONE
BLAKE, AJ
COOK, TA
FORSYTH, AC
GOULD, RO
PATON, RM
[J]. TETRAHEDRON, 1992, 48 (37) : 8053 - 8064
[9] HOW IMPORTANT ARE SECONDARY ORBITAL INTERACTIONS IN FAVORING THE ENDO MODE IN 1,3-DIPOLAR CYCLOADDITIONS OF NITRONES
BURDISSO, M
GANDOLFI, R
GRUNANGER, P
RASTELLI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) : 3427 - 3429
[10] CONTROLLING THE OUTCOME OF A CARBOCATION-INITIATED CYCLIZATION
CHOW, HF
FLEMING, I
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08): : 1815 - 1819

← 1 2 3 4 →