Tandem oxyallylations and retro-ene eliminations. One pot stereoselective synthesis of polypropionate fragments with three contiguous stereogenic centers and one (E)-alkene unit
1997
Abstract
Mixtures of (EE)-2-methyl-1-silyloxypenta-1,3-dienes, enoxysilanes, SO2 and (t-Bu)Me2SiOTf (catalyst) generate (Z)-5-alkyl-1,3-dimethyl-6-oxo-4-silyloxyalk-2-enesulfinic acids that undergo stereoselective retro-ene eliminations of SO2 with the formation of corresponding (E)-3-hydroxy-2-alkyl-4-methylalk-5-en-1-ones with 2,3-syn and 3,4-anti diastereoselectivity. (C) 1997 Elsevier Science Ltd.
Details
Title
Tandem oxyallylations and retro-ene eliminations. One pot stereoselective synthesis of polypropionate fragments with three contiguous stereogenic centers and one (E)-alkene unit
Author(s)
Roulet, J. M. ; Puhr, G. ; Vogel, P.
Published in
Tetrahedron Letters
Volume
38
Issue
35
Pages
6201-6204
Date
1997
ISSN
0040-4039
Keywords
Note
Univ lausanne,chim sect,bch,ch-1015 lausanne,switzerland.
Laboratories
LGSA
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > SB Archives > LGSA - Laboratory of Glycochemistry and Asymmetric Synthesis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date
2005-11-09