铜（II）-双膦催化的烯烃迁移和普林斯环化反应非对映选择性合成取代四氢吡喃
Diastereoselective Synthesis of Substituted Tetrahydropyrans by Copper(II)-Bisphosphine-Catalyzed Olefin Migration and Prins Cyclization.
作者信息
Ghosh Arun K, Kass Jorden, Nicponski Daniel R, Keyes Chad
机构信息
Department of Chemistry and Department of Medicinal Chemistry, Purdue University, West Lafayette, IN 47907, USA, Fax +1(765)4961612.
出版信息
Synthesis (Stuttg). 2012 Dec;44(23):3579-3589. doi: 10.1055/s-0032-1317495.
Abstract
We developed a copper(II) triflate-bisphosphine complex catalyzed olefin migration and Prins cyclization which lead to the synthesis of substituted tetrahydropyran derivatives. The protocol is convenient and a variety of substituted tetrahydropyrans were obtained in good to excellent yields with excellent diastereoselectivities.
摘要
我们开发了一种三氟甲磺酸铜（II）-双膦配合物催化的烯烃迁移和普林斯环化反应，该反应可用于合成取代的四氢吡喃衍生物。该方法简便易行，能够以良好至优异的产率和出色的非对映选择性得到多种取代的四氢吡喃。
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2
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3
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Future Med Chem. 2011 Jul;3(9):1181-97. doi: 10.4155/fmc.11.68.
4
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Antimicrob Agents Chemother. 2011 Apr;55(4):1717-27. doi: 10.1128/AAC.01540-10. Epub 2011 Jan 31.
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J Med Chem. 2011 Jan 27;54(2):622-34. doi: 10.1021/jm1012787. Epub 2010 Dec 31.
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Synlett. 2008 Feb 12;2008(3):363-366. doi: 10.1055/s-2008-1032053.
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J Med Chem. 2010 May 13;53(9):3707-17. doi: 10.1021/jm1001327.
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