通过无痕迹的中心-轴向手性交换，从 1,4-二酮对映选择性合成联苯酚。
Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.
机构信息
Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
出版信息
J Am Chem Soc. 2011 Jan 12;133(1):18-20. doi: 10.1021/ja108717r. Epub 2010 Dec 9.
Abstract
A method for the enantioselective synthesis of biphenols from readily prepared 1,4-diketones is reported. Key to the success of this method is the highly selective transfer of central to axial chirality during a double aromatization event triggered by BF(3)·OEt(2). On the basis of X-ray crystallographic data, a stereochemical model for this chirality exchange process is put forth.
摘要
本文报道了一种从易得的 1,4-二酮制备联苯酚的对映选择性合成方法。该方法的关键是在 BF(3)·OEt(2)引发的双重芳构化反应中，高度选择性地将中心向轴向手性转移。基于 X 射线晶体学数据，提出了这种手性交换过程的立体化学模型。
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