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Enantiopure Derivatives of 1,1,2-Triphenylethane-1,2-diol by Unusual Ring Opening of Its Cyclic Sulfite

✍ Scribed by Fleischer, Ralf ;Galle, Dietmar ;Braun, Manfred

Book ID: 102902521
Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 730 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719970621

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✦ Synopsis

Abstract

The reaction of triphenylglycol (S)‐1 with thionyl chloride leads to the cyclic sulfites 2a and 2b in a ratio of 90:10. When the mixture of diastereomers 2a/b is treated with alcohols 3 or diols 6, enantiomerically pure ethers 5 and 7 are obtained by an unexpected S~N~1‐type ring cleavage. Enantiopure triphenyloxirane (R)‐10 arises under inversion of configuration upon treatment of 2a/b with sodium azide. The configuration of the major diastereomer ~2a~ is determined by NMR spectroscopy and by conversion into the sulfoxide (S)‐15.

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