苄基和烯丙醇直接转化为膦酸酯。
Direct conversion of benzylic and allylic alcohols to phosphonates.
机构信息
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, United States.
出版信息
J Org Chem. 2011 Apr 15;76(8):2875-9. doi: 10.1021/jo200137k. Epub 2011 Mar 15.
Abstract
Benzyl phosphonate esters often serve as reagents in Horner-Wadsworth-Emmons reactions. In most cases, they can be prepared from benzylic alcohols via formation of the corresponding halide followed by an Arbuzov reaction. To identify a more direct synthesis of phosphonate esters, we have developed a one-flask procedure for conversion of benzylic and allylic alcohols to the corresponding phosphonates through treatment with triethyl phosphite and ZnI(2).
摘要
苄基膦酸酯通常可用作 Horner-Wadsworth-Emmons 反应的试剂。在大多数情况下，它们可以通过形成相应的卤化物，然后通过 Arbuzov 反应，从苄基醇制备得到。为了寻找更直接的膦酸酯合成方法，我们开发了一种在一个烧瓶中通过三乙基膦酸酯和 ZnI(2)处理将苄基和烯丙基醇转化为相应的膦酸酯的方法。
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2
Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A.级联环化反应的探索，通过串联芳香取代反应终止：（+）-schweinfurthin A 的全合成。
J Org Chem. 2011 Feb 4;76(3):909-19. doi: 10.1021/jo1022102. Epub 2011 Jan 12.
3
Structural analogues of schweinfurthin F: probing the steric, electronic, and hydrophobic properties of the D-ring substructure.结构类似物的 Schweinfurthin F：探测 D-环亚结构的空间位阻、电子和疏水性。
Bioorg Med Chem. 2010 Feb 15;18(4):1676-83. doi: 10.1016/j.bmc.2009.12.063. Epub 2010 Jan 4.
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