Asymmetric Cycloetherification via the Kinetic Resolution of Alcohols Using Chiral Phosphoric Acid Catalysts

Asymmetric Cycloetherification via the Kinetic Resolution of Alcohols Using Chiral Phosphoric Acid Catalysts
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DOI:
10.1246/cl.160727
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发表时间:
2016-09
期刊:
影响因子:
1.6
通讯作者:
N. Yoneda;A. Matsumoto;K. Asano;S. Matsubara
N. Yoneda;A. Matsumoto;K. Asano;S. Matsubara
中科院分区:
化学4区
文献类型:
--
作者:
N. Yoneda;A. Matsumoto;K. Asano;S. Matsubara

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在本研究中,利用手性磷酸催化剂通过仲醇或叔醇的动力学分解,开发了一种新的不对称环醚化反应,得到了具有两个立体中心的四氢吡喃(THPs)。回收的旋光性醇的环化产生了THPs的其他立体异构体。这些方案为各种光学活性THP衍生物提供了有效的合成途径,这些衍生物是一系列生物活性制剂中发现的重要结构。
In this study, novel asymmetric cycloetherification via the kinetic resolution of secondary or tertiary alcohols using chiral phosphoric acid catalysts was developed, affording tetrahydropyrans (THPs) with two stereogenic centers. The cyclization of the recovered optically active alcohols afforded other stereoisomers of THPs. These protocols offer efficient synthetic routes to various optically active THP derivatives, which are important structures found in a range of biologically active agents.