✦ LIBER ✦

Unusually high asymmetric induction in the pummerer reaction of opticaly active sulfoxides

✍ Scribed by Tatsuo Numata; Osamu Itoh; Shigeru Oae

Book ID: 104238198
Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 128 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)86863-5

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✦ Synopsis

The Pummerer reaction of optically active B-carbonyl substituted alkyl sulfoxides with acetic anhydride in the presence of dicyclohexylcarbodiimide was found to be of highly stereoselective affording the corresponding a-acetoxysulfides with nearly 70% e.e. Among several examples of stereoselective Pummerer reaction of sulfoxides, 1) a few reported examples of asymmetric induction at cl-carbon during the reaction 2) are quite interesting, however, the extent of asymnetric induction was never more than 30% e.e. The low yield of e.e.

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