Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 28, Pages 6150-6154Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402757
Keywords
Nucleophilic addition; Ketoses; C-Glycosides; Lactones; Stereoselectivity
Categories
Funding
- National Natural Science Foundation of China [81102306, 21302068]
- National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China [2012ZX09301001, 2014ZX09507-002]
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Nucleophilic addition of difluoromethyl-2-pyridyl sulfone to sugar lactones proceeded with good yield and excellent stereoselectivity. The hitherto unknown direct addition intermediates are stable and capable of useful conversions: Formal elimination of the anomeric hydroxy and sulfonyl groups yielded a 1-deoxy-1-difluoromethylene mannopyranose derivative. Directly from sugar lactones, by nucleophilic addition and subsequent one-pot reduction with allylmagnesium chloride, unprecedented fluorinated 2-ketose analogues were prepared efficiently.
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