α-Ketophosphonates as ester surrogates: isothiourea-catalyzed asymmetric diester and lactone synthesis

Siobhan R Smith; Stuart M Leckie; Reuben Holmes; James Douglas; Charlene Fallan; Peter Shapland; David Pryde; Alexandra M Z Slawin; Andrew D Smith

doi:10.1021/ol500873s

α-Ketophosphonates as ester surrogates: isothiourea-catalyzed asymmetric diester and lactone synthesis

Org Lett. 2014 May 2;16(9):2506-9. doi: 10.1021/ol500873s. Epub 2014 Apr 15.

Authors

Siobhan R Smith¹, Stuart M Leckie, Reuben Holmes, James Douglas, Charlene Fallan, Peter Shapland, David Pryde, Alexandra M Z Slawin, Andrew D Smith

Affiliation

¹ EaStCHEM, School of Chemistry, University of St. Andrews , North Haugh, St. Andrews KY16 9ST, U.K.

PMID: 24734989
DOI: 10.1021/ol500873s

Abstract

Isothiourea HBTM-2.1 catalyzes the asymmetric Michael addition/lactonization of aryl- and alkenylacetic acids using α-keto-β,γ-unsaturated phosphonates as α,β-unsaturated ester surrogates, giving access to a diverse range of stereodefined lactones or enantioenriched functionalized diesters upon ring-opening.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetates / chemistry
Catalysis
Esters
Lactones / chemical synthesis*
Lactones / chemistry
Molecular Structure
Organophosphonates / chemistry*
Thiourea / chemistry*

Substances

Acetates
Esters
Lactones
Organophosphonates
Thiourea