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β,γ-efoxy sulfones in organic synthesis. Part 2: Preparation of β,γ-bifunctionalized sulfones

✍ Scribed by Carmen Nájera; José M. Sansano

Book ID
104204383
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
664 KB
Volume
47
Category
Article
ISSN
0040-4020

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✦ Synopsis

Heteronucleophiles reagents react with &y-epoxy sulfones 1 at the y-position in the presence of Ti(OPf), or magnesium halides to afford regioselectively y-functionalixed @-hydroxy sulfones 2. With soft nucleofiles such as sodium axide, triphenylphosphine, or sodium benxethiolate the reaction takes place in the absence of Lewis acids. In the case of basic reagents such as sodium me&oxide or diethylamine the corresponding regioisomers, the /3functionalixed y-hydroxy sulfones 3 were exclusively obtained. The preparation of compounds 3 (R*=H) was also carried out starting from 3-tosyl-2-propen-l-o1

(4) by Michael addition of different heteronucleophiles.

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