Lewis acid activated synthesis of highly substituted cyclopentanes by the N-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters.
作者信息
Cohen Daniel T, Cardinal-David Benoit, Scheidt Karl A
机构信息
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA.
出版信息
Angew Chem Int Ed Engl. 2011 Feb 11;50(7):1678-82. doi: 10.1002/anie.201005908. Epub 2011 Jan 14.
Abstract
摘要
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2
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Nat Chem. 2010 Mar;2(3):167-78. doi: 10.1038/nchem.539. Epub 2010 Feb 19.
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Aldrichimica Acta. 2009;42(3):55-66.
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Org Biomol Chem. 2010 Nov 7;8(21):4884-91. doi: 10.1039/c0ob00088d. Epub 2010 Aug 26.
6
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J Am Chem Soc. 2009 Sep 30;131(38):13606-7. doi: 10.1021/ja906472m.
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