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Highly Stereoselective Nucleophilic Addition of Difluoromethyl‐2‐pyridyl Sulfone to Sugar Lactones and Efficient Synthesis of Fluorinated 2‐Ketoses
Author(s) -
Liu Xiao,
Yin Qiang,
Yin Jian,
Chen Guohua,
Wang Xin,
You QiDong,
Chen YueLei,
Xiong Bing,
Shen Jingkang
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402757
Subject(s) - chemistry , stereoselectivity , sulfone , nucleophile , anomer , ketose , nucleophilic addition , organic chemistry , yield (engineering) , sulfonyl , sugar , medicinal chemistry , aldose , catalysis , glycoside , materials science , alkyl , metallurgy
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.