环状乙烯基砜向重排乙烯基膦酸酯的转化。

Conversion of cyclic vinyl sulfones to transposed vinyl phosphonates.

作者信息

Noshi Mohammad N, El-awa Ahmad, Torres Eduardo, Fuchs Philip L

机构信息

Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, USA.

出版信息

J Am Chem Soc. 2007 Sep 12;129(36):11242-7. doi: 10.1021/ja072890p. Epub 2007 Aug 16.

DOI:10.1021/ja072890p

PMID:17696536

Abstract

Functionalized cyclic vinyl sulfones were directly converted to the "polarity reversed" vinyl phosphonates through an efficient one pot procedure. Ozonolysis of these vinyl sulfones and vinyl phosphonates furnish complementary sets of termini-differentiated ester-aldehydes. This strategy has been applied for preparation of segments needed for the synthesis of Aplyronine A. The scope and limitations of this transformation were defined.

摘要

官能化的环状乙烯基砜通过高效的一锅法直接转化为“极性反转”的乙烯基膦酸酯。这些乙烯基砜和乙烯基膦酸酯的臭氧分解提供了互补的末端分化酯醛类化合物。该策略已应用于制备海兔毒素A合成所需的片段。定义了这种转化的范围和局限性。