TANDEM OXYALLYLATIONS AND RETRO-ENE ELIMINATIONS - ONE-POT STEREOSELECTIVE SYNTHESIS OF POLYPROPIONATE FRAGMENTS WITH 3 CONTIGUOUS STEREOGENIC CENTERS AND ONE (E)-ALKENE UNIT

Authors
ROULET JM PUHR G VOGEL P
Citation
Jm. Roulet et al., TANDEM OXYALLYLATIONS AND RETRO-ENE ELIMINATIONS - ONE-POT STEREOSELECTIVE SYNTHESIS OF POLYPROPIONATE FRAGMENTS WITH 3 CONTIGUOUS STEREOGENIC CENTERS AND ONE (E)-ALKENE UNIT, Tetrahedron letters, 38(35), 1997, pp. 6201-6204
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
35
Year of publication
1997
Pages
6201 - 6204
Database
ISI
SICI code
0040-4039(1997)38:35<6201:TOARE->2.0.ZU;2-8
Abstract
Mixtures of (EE)-2-methyl-1-silyloxypenta-1,3-dienes, enoxysilanes, SO 2 and (t-Bu)Me2SiOTf (catalyst) generate kyl-1,3-dimethyl-6-oxo-4-sily loxyalk-2-enesulfinic acids that undergo stereoselective retro-ene eli minations of SO2 with the formation of corresponding (E)-3-hydroxy-2-a lkyl-4-methylalk-5-en-1-ones with 2,3-syn and 3,4-anti diastereoselect ivity. (C) 1997 Elsevier Science Ltd.