Self-catalytic Michael reaction of enolizable carbonyl compounds. A facile route to α-methylene-δ-valerolactones

Various dicyclohexylammonium 2-phosphono-5-oxoalkanoates 3 were prepared by the Michael reaction of enolizable carbonyl compounds with the acrylate 1 . The corresponding 2-phosphono-5-oxoalkanoic acids 4 were converted into α-phosphono-δ-valerolactones 6 . The products were shown to be useful substr...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2003-11, Vol.59 (46), p.9199-9211
Main Authors: Krawczyk, Henryk, Śliwiński, Marcin
Format: Article
Language:English
Subjects:
5-oxoalkanoic acids
Michael reaction
α-methylene-δ-valerolactones
α-phosphonolactones
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Various dicyclohexylammonium 2-phosphono-5-oxoalkanoates 3 were prepared by the Michael reaction of enolizable carbonyl compounds with the acrylate 1 . The corresponding 2-phosphono-5-oxoalkanoic acids 4 were converted into α-phosphono-δ-valerolactones 6 . The products were shown to be useful substrates for the synthesis of α-methylene-δ-valerolactones 7 by the Horner–Wadsworth–Emmons reaction. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2003.09.039