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ALTERNATIVE AND COMPLEMENTARY SYNTHETIC APPROACHES TO ╬▓ CARBOXY-╬▒-METHYLENE-╬│-BUTYROLACTONE ETHYL ESTERS
STRAT├ëGIES DE SYNTH├łSE ALTERNATIVES POUR L'├ëCHAFAUDAGE D'ESTERS ├ëTHYLIQUES DE ╬▓ CARBOXY-╬▒-M├ëTHYL├łNE-╬│-BUTYROLACTONES


GWENA├őLLE LIBERGE 1, 2, STEPHANE LEBRUN 1, 2, AXEL COUTURE 1, 3 ANDPIERRE GRANDCLAUDON 1, 2*
1. Universit├ę Lille Nord de France, F-59000 Lille, France
2. USTL, Laboratoire de Chimie Organique Physique, EA CMF 4478, Bâtiment C3(2), F-59655 Villeneuve d'Ascq, France
3.CNRS, UMR 8181 'UCCS', F-59655 Villeneuve d'Ascq, France
*Corresponding author: pierre.grandclaudon@univ-lille1.fr

Issue:

SCSCC6, Volume XII, No. 4

Section:

Volume XII, No. 4(2011)

Abstract:

Alternative synthetic approaches to a variety of ╬▓ substituted and carboxylated ╬▒-methylene-╬│-butyrolactones have been developed. In the first approach the mandatory methylene unit was incorporated on precursor compounds at early stage of the synthesis on reliance with Horner-Emmons protocol. In the alternative approach which further tolerates multifarious substituents at ╬│-position of the lactone template the unsaturated moiety ╬▒ to the lactone carbonyl group is connected at a later stage through a deprotonation / methoxymethylation / elimination sequence.

Keywords:

cyclization, elimination, enolate, lactones, transesterification, Wadsworth-Emmons reaction.

Code [ID]:

CSCC6201104V04S01A0003 [0003427]

Full paper:

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