Transition-metal catalyzed synthesis of delta-hydroxy-gamma-lactones from bis(trimethylsilyl) ketene acetals and allylic acetates via gamma-unsaturated carboxylic acids. Comments on the formation of alpha-cyclopropyl carboxylic acids

Authors
Rudler, H Harris, P Parlier, A Cantagrel, F Denise, B Bellassoued, M Vaissermann, J
Citation
H. Rudler et al., Transition-metal catalyzed synthesis of delta-hydroxy-gamma-lactones from bis(trimethylsilyl) ketene acetals and allylic acetates via gamma-unsaturated carboxylic acids. Comments on the formation of alpha-cyclopropyl carboxylic acids, J ORGMET CH, 624(1-2), 2001, pp. 186-202
Citations number
61
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANOMETALLIC CHEMISTRY
ISSN journal
0022328X → ACNP
Volume
624
Issue
1-2
Year of publication
2001
Pages
186 - 202
Database
ISI
SICI code
0022-328X(20010401)624:1-2<186:TCSODF>2.0.ZU;2-V
Abstract
Bis(trimethylsilyl)ketene acetals react with allylic acetates in the presen ce of Pd(0) complexes to give gamma -unsaturated carboxylic acids together with alpha -cyclopropyl carboxylic acids. The unsaturated acids can be conv erted catalytically to delta -hydroxy-gamma -lactones by the: H2O2/MTO syst em (methyltrioxorhenium) and to butenolides by Pd(II) catalyzed intramolecu lar cyclization reactions. The structure of two of these lactones has been established by X-ray analysis. The mechanism of the formation of the cyclop ropanic acids will be discussed. (C) 2001 Elsevier Science B.V. All rights reserved.