1,3-Dipolar cycloaddition of 2-azetidinone-tethered azomethine ylides. Application to the rapid, stereocontrolled synthesis of optically pure highly functionalised pyrrolizidine systems

被引：26

作者：

Alcaide, B ^{[1
]}

Almendros, P ^{[1
]}

Alonso, JM ^{[1
]}

Aly, MF ^{[1
]}

机构：

[1] Univ Complutense Madrid, Fac Ciencias Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

来源：

CHEMICAL COMMUNICATIONS | 2000年 / 06期

关键词：

D O I：

10.1039/b000249f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new straightforward methodology to prepare polyfunctionalised enantiopure pyrrolizidine systems, based on the 1,3-dipolar cycloaddition of 2-azetidinone-tethered azomethine ylides as the key reaction, is presented.

引用

页码：485 / 486

页数：2

共 22 条

[1] Diastereoselective Baylis-Hillman reaction of 4-oxoazetidine-2-carbaldehydes:: rapid, stereocontrolled and divergent radical synthesis of highly functionalised β-lactams fused to medium rings
Alcaide, B
Almendros, P
Aragoncillo, C
[J]. CHEMICAL COMMUNICATIONS, 1999, (18) : 1913 - 1914
[2] Stereoselective synthesis of fused bicyclic β-lactams through radical cyclization of enyne-2-azetidinones
Alcaide, B
Rodríguez-Campos, IM
Rodríguez-López, J
Rodríguez-Vicente, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) : 5377 - 5387
[3] C4,C4'-bis-beta-lactam to fused bis-gamma-lactam rearrangement
Alcaide, B
MartinCantalejo, Y
PerezCastells, J
Sierra, MA
Monge, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9156 - 9163
[4] New synthesis of fused tricyclic 2-azetidinones using stereoselective allylation of cis-4-formyl-β-lactams and intramolecular Diels-Alder reaction
Alcaide, B
Almendros, P
[J]. TETRAHEDRON LETTERS, 1999, 40 (05) : 1015 - 1018
[5] THE STEREOSELECTIVE PREPARATION OF MONO-BETA-LACTAMS AND BIS-BETA-LACTAMS BY THE 1,4-DIAZA 1,3-DIENE-ACID CHLORIDE CONDENSATION - SCOPE AND SYNTHETIC APPLICATIONS
ALCAIDE, B
MARTINCANTALEJO, Y
PEREZCASTELLS, J
RODRIGUEZLOPEZ, J
SIERRA, MA
MONGE, A
PEREZGARCIA, V
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) : 5921 - 5931
[6] [Anonymous], 1995, ADV ASYMMETRIC SYNTH
[7] [Anonymous], 1993, ORGANIC CHEM BETA LA
[8] Broggini G, 1999, SYNTHESIS-STUTTGART, P905
[9] PYRROLIZIDINES BY REARRANGEMENT OF BETA-LACTAMS
CAVAGNA, F
LINKIES, A
PIETSCH, H
REUSCHLING, D
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (02): : 129 - 130
[10] Georg G. I., 1993, The Organic Chemistry of (3-Lactams, P295, DOI [10.1002/chin.199425299, DOI 10.1002/CHIN.199425299]

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