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奎尼丁硫脲催化的β-硝基膦酸酯对映选择性合成:分子筛的有益作用

Quinidine thiourea-catalyzed enantioselective synthesis of β-nitrophosphonates: Beneficial effects of molecular sieves.

作者信息

Abbaraju Santhi, Bhanushali Mayur, Zhao Cong-Gui

机构信息

Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249, USA.

出版信息

Tetrahedron. 2011 Sep 30;67(39):7479-7484. doi: 10.1016/j.tet.2011.07.059.

Abstract

An efficient method for enantioselective synthesis of β-nitrophosphonates via the Michael addition of diphenyl phosphite to nitroalkenes using the readily available quinidine thiourea organocatalyst has been developed. The desired β-nitrophosphonates were obtained in good ee values. Molecular sieves were found to be crucial for achieving high reproducible yields in this reaction.

摘要

已经开发出一种有效的方法,通过使用易于获得的奎尼丁硫脲有机催化剂,使亚磷酸二苯酯与硝基烯烃进行迈克尔加成反应,对映选择性合成β-硝基膦酸酯。以良好的对映体过量值获得了所需的β-硝基膦酸酯。发现分子筛对于在该反应中实现高重现性产率至关重要。

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Organocatalytic High Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates.
Adv Synth Catal. 2011 Jun 30;353(10):1729-1734. doi: 10.1002/adsc.201000835.
2
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Org Biomol Chem. 2011 Apr 21;9(8):2777-83. doi: 10.1039/c0ob01059f. Epub 2011 Feb 25.
4
Squaramide-catalyzed enantioselective Michael addition of diphenyl phosphite to nitroalkenes.
Angew Chem Int Ed Engl. 2010;49(1):153-6. doi: 10.1002/anie.200904779.
5
Aerobic photooxidation of phosphite esters using diorganotelluride catalysts.
Org Lett. 2009 May 7;11(9):1879-81. doi: 10.1021/ol900240s.
7
A diastereo- and enantioselective synthesis of alpha-substituted anti-alpha,beta-diaminophosphonic acid derivatives.
Chem Commun (Camb). 2008 Sep 21(35):4177-9. doi: 10.1039/b808393b. Epub 2008 Aug 6.
8
Enantioselective synthesis of alpha-aminopropargylphosphonates.
Tetrahedron Lett. 2007 Jun 18;48(25):4339-4342. doi: 10.1016/j.tetlet.2007.04.124.
9
Asymmetric Friedel-Crafts alkylation of pyrroles with nitroalkenes using a dinuclear zinc catalyst.
J Am Chem Soc. 2008 Feb 27;130(8):2438-9. doi: 10.1021/ja711080y. Epub 2008 Feb 1.
10
Enantioselective 1,4-addition reactions of diphenyl phosphite to nitroalkenes catalyzed by an axially chiral guanidine.
J Am Chem Soc. 2007 Nov 21;129(46):14112-3. doi: 10.1021/ja0746619. Epub 2007 Oct 26.

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