Tandem oxyallylations and retro-ene eliminations. One pot stereoselective synthesis of polypropionate fragments with three contiguous stereogenic centers and one (E)-alkene unit

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.


Published in:
Tetrahedron Letters, 38, 35, 6201-6204
Year:
1997
ISSN:
0040-4039
Keywords:
Note:
Univ lausanne,chim sect,bch,ch-1015 lausanne,switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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