Highly Stereoselective Nucleophilic Addition of Difluoromethyl‐2‐pyridyl Sulfone to Sugar Lactones and Efficient Synthesis of Fluorinated 2‐Ketoses1. Issue 28 (29th August 2014)

• Record Type: Journal Article
• Authors: Liu, Xiao; Yin, Qiang; Yin, Jian; Chen, Guohua; Wang, Xin; You, Qi‐Dong; Chen, Yue‐Lei; Xiong, Bing; Shen, Jingkang
• Is Part Of: European journal of organic chemistry. Issue 28(2014)
• Page Start: 6150
• Page End: 6154
• Publication Date: 2014-08-29
• Subjects: Nucleophilic addition -- Ketoses -- C‐Glycosides -- Lactones -- Stereoselectivity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402757
• Languages: English
• ISSNs: 1434-193X

Abstract

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.