Solid-phase access to polyhydroxypyrrolizidines by 1,3-dipolar cycloaddition of (S)-3-alkoxypyrroline N-oxide to maleate and crotonate derivatives

被引：21

作者：

Pisaneschi, F ^{[1
]}

Della Monica, C ^{[1
]}

Cordero, FM ^{[1
]}

Brandi, A ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim Organ Ugo Schiff, Polo Sci, I-50019 Sesto Fiorentino, FI, Italy

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 33期

关键词：

solid-phase synthesis; 1,3-dipolar cycloaddition; nitrone; pyrrolizidines;

D O I：

10.1016/S0040-4039(02)01208-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,7-Dihydroxyhexahydropyrrolizine-1-carboxylic acid derivatives have been prepared in solid-phase by intermolecular 1,3-dipolar cycloaddition between an immobilised malcate or 4-hydroxycrotonate and an enantiopure 3-alkoxypyrroline N-oxide. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5711 / 5714

页数：4

共 50 条

[1] Solid-phase synthesis of functionalized tropane derivatives via 1,3-dipolar cycloaddition
Caix-Haumesser, S
Hanna, I
Lallemand, JY
Peyronel, JF
TETRAHEDRON LETTERS, 2001, 42 (22) : 3721 - 3723
[2] THE 1,3-DIPOLAR CYCLOADDITION OF 3-METHYL-5-PHENYLISOXAZOLINE N-OXIDE
CHOW, YL
SHU, YY
BAKKER, BH
PILLAY, KS
HETEROCYCLES, 1989, 29 (12) : 2245 - 2248
[3] Intramolecular 1,3-Dipolar Cycloaddition of Nitrile N-Oxide Accompanied by Dearomatization
Yonekawa, Morio
Koyama, Yasuhito
Kuwata, Shigeki
Takata, Toshikazu
ORGANIC LETTERS, 2012, 14 (04) : 1164 - 1167
[4] Stereodivergent approach to enantiopure hydroxyindolizidines through 1,3-dipolar cycloaddition of 3-hydroxypyrroline N-oxide derivatives
Cordero, FM
Pisaneschi, F
Gensini, M
Goti, A
Brandi, A
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (12) : 1941 - 1951
[5] 1,3-DIPOLAR CYCLOADDITION OF N-OXIDE WITH 2-METHYLENE-1,3-DITHIANE
YAMAMOTO, M
SUENAGA, T
SUZUKI, K
NARUCHI, K
YAMADA, K
HETEROCYCLES, 1987, 26 (03) : 755 - 758
[6] 1,3-DIPOLAR CYCLOADDITION REACTION OF AROMATIC N-OXIDE WITH HEXAFLUOROBUTYNE-2
KOBAYASHI, Y
KUMADAKI, I
FUJINO, S
HETEROCYCLES, 1977, 7 : 871 - 876
[7] 1,3-DIPOLAR CYCLOADDITION BETWEEN ETHYL TRIFLUOROACETOACETATE AND N-(BENZYLIDENE)METHYLAMINE N-OXIDE
BEGUE, JP
BONNETDELPON, D
LEQUEUX, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11): : 2888 - 2889
[8] 1,3-Dipolar cycloaddition of 1-substituted 3,3,3-trifluoropropenes to ethyl cyanocarboxylate N-oxide
Yuriy N. Markitanov
Vadim M. Timoshenko
Yuriy G. Shermolovich
Chemistry of Heterocyclic Compounds, 2018, 54 : 89 - 92
[9] Solid-phase synthesis of cleavable N-arylmaleimides:: Applications in 1,3-dipolar cycloaddition and in thiol scavenging
Hoveyda, HR
Hall, DG
ORGANIC LETTERS, 2001, 3 (22) : 3491 - 3494
[10] 1,3-Dipolar cycloaddition of 1-substituted 3,3,3-trifluoropropenes to ethyl cyanocarboxylate N-oxide
Markitanov, Yuriy N.
Timoshenko, Vadim M.
Shermolovich, Yuriy G.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (01) : 89 - 92

← 1 2 3 4 5 →