Easy access to alpha-aryl substituted gamma-ketophosphonates: lewis acid mediated reactions of 1,3-diketones with alpha-hydroxyphosphonates and tandem regioselective C-C bond cleavage

TitleEasy access to alpha-aryl substituted gamma-ketophosphonates: lewis acid mediated reactions of 1,3-diketones with alpha-hydroxyphosphonates and tandem regioselective C-C bond cleavage
Publication TypeJournal Article
Year of Publication2014
AuthorsPallikonda, G, Chakravarty, M, Sahoo, MKumar
JournalOrganic & Biomolecular Chemistry
Volume12
Issue36
Pagination7140-7149
Date PublishedJUL
Type of ArticleArticle
ISSN1477-0520
Abstract

A range of alpha-aryl substituted gamma-ketophosphonates is synthesised by Lewis acid mediated reactions of 1,3-diketones and easily accessible, inexpensive benzylic alpha-hydroxyphosphonates in an operationally simple method under solvent-free conditions without exclusion of air/moisture. A regioselective C-C bond cleavage for 1,3-diketones in a tandem fashion has also been demonstrated. Synthesis of a gamma-ketophosphonate with phenol functionality at the a-position (structural analogue of raspberry ketone, a natural product) has also been presented.

DOI10.1039/c4ob01091d
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.559

Divison category: 
Catalysis and Inorganic Chemistry