二硼甲烷的立体选择性串联双亲电偶联反应。
Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.
机构信息
Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
出版信息
J Am Chem Soc. 2017 Oct 11;139(40):14061-14064. doi: 10.1021/jacs.7b09309. Epub 2017 Sep 27.
Abstract
A copper-catalyzed three-component linchpin coupling method for the stereoselective union of readily available epoxides and allyl electrophiles is disclosed. Transformations employ [B(pin)]-methane as a conjunctive reagent, resulting in the formation of two C-C bonds at a single carbon center bearing a C(sp) organoboron functional group. Products are obtained in 42-99% yield, and up to >20:1 dr. The utility of the approach is highlighted by stereospecific transformations entailing allylation, tandem cross coupling, and application to the synthesis 1,3-polyol motifs.
摘要
本文公开了一种铜催化的三组分关键偶联方法，用于立体选择性地构建易得的环氧化物和烯丙基亲电试剂。该转化采用 [B(pin)]-甲烷作为连接试剂，在一个单碳中心形成两个 C-C 键，该碳中心带有 C(sp)有机硼官能团。产物的产率为 42-99%，dr 值最高可达>20:1。该方法的实用性通过立体特异性转化得到了突出体现，包括烯丙基化、串联交叉偶联以及应用于 1,3-多醇基序的合成。
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