De novo asymmetric syntheses of C-4-substituted sugars via an iterative dihydroxylation strategy

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• 作者：Md. Moinuddin Ahmed and George A. O’ ; Doherty
• 关键词：Diastereoselective dihydroxylation ; Fluorosugars ; Deoxysugars ; Asymmetric synthesis
• 刊名：Carbohydrate Research
• 出版年：2006
• 出版时间：24 July 2006
• 年：2006
• 卷：341
• 期：10
• 页码：1505-1521
• 全文大小：289 K

文摘

A short and highly efficient route to various C-4 substituted sugar lactones has been developed. The key to the overall transformation is the sequential osmium-catalyzed dihydroxylation reaction of substituted 2,4-dienoates and an allylic substitution at the C-4 position. When the Sharpless AD-mix procedure is used in a matched sense for the second dihydroxylation reaction, it results in an exceedingly diastereo- and enantioselective synthesis of several C-4-substituted sugars.