First example of a third generation nitrone cycloaddition

被引：17

作者：

deMarch, P

Figueredo, M

Font, J

Milan, S

AlvarezLarena, A

Piniella, JF

Molins, E

机构：

[1] UNIV AUTONOMA BARCELONA,UNITAT CRISTAL IOGRAFIA,E-08193 BARCELONA,SPAIN

[2] CSIC,INST CIENCIA MAT,E-08193 BARCELONA,SPAIN

来源：

TETRAHEDRON | 1997年 / 53卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(96)01177-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Compounds 5 and 6, derived from the cycloadditions of a nitrone to alpha,beta-unsaturated lactones, were oxidized with m-chloroperbenzoic acid affording regiospecifically aldonitrones, 8 and 14, respectively. These second generation nitrones were reacted with several dipolarophiles yielding cycloadducts 9-13, 15, and 16. A repeated sequence of oxidation-cycloaddition applied to compound 12 allowed the isolation of the first example of a third generation cycloadduct, 17. During this work a series of new highly functionalized pyrrolidines have been prepared. (C) 1997 Elsevier Science Ltd.

引用

页码：2979 / 2988

页数：10

共 13 条

[1] CYCLOADDITION OF 5-SUBSTITUTED 1-PYRROLINE 1-OXIDE AND CONVERSION OF THE NITRONE CYCLOADDUCTS INTO CIS-2,5-DISUBSTITUTED AND TRANS-2,5-DISUBSTITUTED PYRROLIDINES
ALI, SA
WAZEER, MIM
[J]. TETRAHEDRON, 1993, 49 (20) : 4339 - 4354
[2] ALI SA, 1993, TETRAHEDRON LETT, V34, P5325
[3] PERACID INDUCED RING-OPENING OF ISOXAZOLIDINES - A MECHANISTIC STUDY
ALI, SA
WAZEER, MIM
[J]. TETRAHEDRON LETTERS, 1992, 33 (22) : 3219 - 3222
[4] NITRONE CYCLOADDITION - PERACID OXIDATION OF PERHYDRO-1,2-OXAZOLO[3,2-C][1,4]OXAZINES
ALI, SA
ALMUALLEM, HA
[J]. TETRAHEDRON, 1993, 49 (33) : 7373 - 7384
[5] CYCLOADDITION REACTIONS OF 3,4-DIHYDRO-2H-PYRROLE 1-OXIDE WITH ALPHA,BETA-UNSATURATED LACTONES
ALONSOPERARNAU, D
DEMARCH, P
FIGUEREDO, M
FONT, J
SORIA, A
[J]. TETRAHEDRON, 1993, 49 (20) : 4267 - 4274
[6] Diastereofacial selectivity in the cycloaddition of nitrones to(E)-gamma-oxygenated alpha,beta-unsaturated esters
Busque, F
deMarch, P
Figueredo, M
Font, J
Monsalvatje, M
Virgili, A
AlvarezLarena, A
Piniella, JF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) : 8578 - 8585
[7] NITRONE CYCLOADDITION - AN APPROACH TO THE CYCLOPHANE ALKALOID (+/-)-LYTHRANIDINE
CARRUTHERS, W
COGGINS, P
WESTON, JB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (03): : 611 - 616
[8] DEMARCH P, 1995, RECL TRAV CHIM PAY B, V114, P357
[9] EPIMERIC SYN-BICYCLO(3.2.1)OCTANE-2,8-DIOLS
LEBEL, NA
SPURLOCK, LA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (06) : 1337 - &
[10] NAKAGAWA M, 1974, SYNTHESIS-STUTTGART, P510

← 1 2 →