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Stereoselective Synthesis of Enantiomerically Pure β-Fluoroalkyl γ-Butyrolactones by Sulfoxide-Directed Lactonization
- Source :
- European Journal of Organic Chemistry. 1999:111-115
- Publication Year :
- 1999
- Publisher :
- Wiley, 1999.
-
Abstract
- Enantiomerically pure α,α-dichloro β-fluoroalkyl γ-p-tolylthio γ-butyrolactones trans-6a–c have been obtained with excellent stereocontrol (> 98:2) and enantiomeric purity (> 98:2) by sulfoxide-directed lactonization (Marino's annu-lation reaction) of β-fluoroalkyl vinyl sulfoxides (R)-(E)-5a–c with dichloroketene. Highly chemoselective dechlorination and desulfurization reactions performed on trans-6c efficiently provided the β-chlorodifluoromethyl γ-butyrolactone (S)-8c, the absolute stereochemistry of which was determined by X-ray diffraction analysis of its γ-p-tolylthio precursor (2R,3S)-7c.
Details
- ISSN :
- 10990690 and 1434193X
- Volume :
- 1999
- Database :
- OpenAIRE
- Journal :
- European Journal of Organic Chemistry
- Accession number :
- edsair.doi...........e388bcfc1116bc9747e9fab29e2dcfdb