Nickel-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones.
作者信息
Thakur Ashish, Facer Megan E, Louie Janis
机构信息
Department of Chemistry, University of Utah, 315 South, 1400 East, Salt Lake City, Utah 84112-0850 (USA) http://www.chem.utah.edu/directory/faculty/louie.html.
出版信息
Angew Chem Int Ed Engl. 2013 Nov 11;52(46):12161-5. doi: 10.1002/anie.201306869. Epub 2013 Sep 23.
Abstract
摘要
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1
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2
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Angew Chem Int Ed Engl. 1999 Feb 1;38(3):397-400. doi: 10.1002/(SICI)1521-3773(19990201)38:3<397::AID-ANIE397>3.0.CO;2-Y.
3
Vinylcyclopropane derivatives in transition-metal-catalyzed cycloadditions for the synthesis of carbocyclic compounds.
J Org Chem. 2013 Jul 19;78(14):6842-8. doi: 10.1021/jo400609w. Epub 2013 Jun 25.
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5
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J Am Chem Soc. 2013 May 15;135(19):7142-5. doi: 10.1021/ja403461f. Epub 2013 May 3.
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8
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9
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