通过β-氯-α-碘-α,β-不饱和酯的区域选择性和立体特异性钯催化偶联反应制备单异构体四取代烯烃。
Single-isomer tetrasubstituted olefins from regioselective and stereospecific palladium-catalyzed coupling of beta-chloro-alpha-iodo-alpha,beta-unsaturated esters.
作者信息
Lemay Alison B, Vulic Katarina S, Ogilvie William W
机构信息
Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.
出版信息
J Org Chem. 2006 Apr 28;71(9):3615-8. doi: 10.1021/jo060144h.
The efficient regioselective and stereospecific synthesis of tetrasubstituted olefins using a mild and convenient method is disclosed. 2-Alkynyl esters are selectively converted to E-beta-chloro-alpha-iodo-alpha,beta-unsaturated esters by exposure to Bu4NI in refluxing dichloroethane. These products are produced cleanly, regio- and stereoselectively, and in high yields. Single-isomer tetrasubstituted olefins bearing four different carbon substituents are then synthesized by sequential palladium-catalyzed coupling reactions. Selectivity results from reactivity differences in the intermediate substrates.
公开了一种使用温和且便捷的方法高效地进行区域选择性和立体选择性合成四取代烯烃的方法。通过在回流的二氯乙烷中暴露于四丁基碘化铵，2-炔基酯被选择性地转化为E-β-氯-α-碘-α,β-不饱和酯。这些产物能够以区域和立体选择性的方式干净地生成，并且产率很高。然后通过连续的钯催化偶联反应合成带有四个不同碳取代基的单异构体四取代烯烃。选择性源于中间底物的反应性差异。
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