X=Y=ZH systems as potential 1,3-dipoles. Part 62: 1,3-Dipolar cycloaddition reactions of metallo-azomethine ylides derived from alpha-iminophosphonates

Metallo-azomethine ylides, generated from iminophosphonates in combination with LiBr or AgOAc and bases Et3N, DBU, t-butyl tetramethylguanidine(BTMG) undergo cycloaddition to give dialkyl pyrrolidine-2-phosphonates along with the corresponding Michael adduct in some cases. Cycloadditions with the ch...

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Bibliographic Details
Published inTetrahedron Vol. 61; no. 45; pp. 10667 - 10682
Main Authors Dondas, HA, Durust, Y, Grigg, R, Slater, MJ, Sarker, MAB
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 07.11.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
cycloaddition
azomethine ylide
2-PI COMPONENTS
ACIDS
iminophosphonate metallo-dipole
IMINES
2-OXOINDOLIN-3-YLIDENE DERIVATIVES
AMINO ESTERS
CATALYSTS
Y-ZH SYSTEMS
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Summary:Metallo-azomethine ylides, generated from iminophosphonates in combination with LiBr or AgOAc and bases Et3N, DBU, t-butyl tetramethylguanidine(BTMG) undergo cycloaddition to give dialkyl pyrrolidine-2-phosphonates along with the corresponding Michael adduct in some cases. Cycloadditions with the chiral dipolarophile 5R-(1'R,2'S,5'R-menthyloxy)-2-(5H)-furanone (MOF) afforded enantiopure cycloadducts. (c) 2005 Elsevier Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/j.tet.2005.08.079