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

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

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.

Citation

Smith , S R , Leckie , S M , Holmes , R , Douglas , J , Fallan , C , Shapland , P , Pryde , D , Slawin , A M Z & Smith , A D 2014 , ' alpha-Ketophosphonates as ester surrogates : isothiourea-catalyzed asymmetric diester and lactone synthesis ' , Organic Letters , vol. 16 , no. 9 , pp. 2506-2509 . https://doi.org/10.1021/ol500873s

Publication

Organic Letters

Status

Peer reviewed

DOI

https://doi.org/10.1021/ol500873s

ISSN

1523-7060

Type

Journal article

Rights

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © 2014 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol500873s

Description

This work is in part supported by the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/6480

St Andrews Research Repository