4-Acetoxy- and 4-Cyano-1,3-Dioxanes in Synthesis

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• 作者：Christopher J. Sinz ; Scott D. Rychnovsky
• 关键词：Cyanohydrin acetonide alkylations ; Reductive decyanations ; Oxocarbenium ions ; Reductive lithiation
• 刊名：Topics in Current Chemistry
• 出版年：2001
• 出版时间：2001
• 年：2001
• 卷：216
• 期：1
• 页码：pp.51-92
• 全文大小：603 KB
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Organic Chemistry
  Inorganic Chemistry
  Theoretical and Computational Chemistry
  Medicinal Chemistry
  Biochemistry
  Organometallic Chemistry
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1436-5049

文摘

Alkylations of 4-cyano-1,3-dioxanes (cyanohydrin acetonides) represent a highly practical approach to syn-1,3-diol synthesis. Herein we present a comprehensive summary of cyanohydrin acetonide chemistry, with particular emphasis on practical aspects of couplings, as well as their utility in natural product synthesis. Both 4-acetoxy-1,3-dioxanes and 4-lithio-1,3-dioxanes have emerged as interesting anti-1,3-diol synthons. The preparation and utility of these two synthons are described.