Highly Stereoselective Nucleophilic Addition of Difluoromethyl‐2‐pyridyl Sulfone to Sugar Lactones and Efficient Synthesis of Fluorinated 2‐Ketoses1. Issue 28 (29th August 2014) - Liu, Xiao
Abstract: 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. Abstract : Nucleophilic addition of difluoromethyl‐2‐pyridyl sulfone to sugar lactones gave intermediates that are stable and capable of useful conversions. Formal elimination of the anomeric hydroxy and sulfonyl groups yielded a 1‐deoxy‐1‐difluoromethylene mannopyranose derivative. Fluorinated 2‐ketose analogues were prepared by a one‐pot reduction with allylmagnesium chloride.