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Catalytic Enantioselective Intermolecular Cycloaddition of Diazodiketoester-Derived Carbonyl Ylides with Indoles Using Chiral Dirhodium(II) Carboxylates

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Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
Cite this: Org. Lett. 2011, 13, 23, 6284–6287
Publication Date (Web):November 2, 2011
https://doi.org/10.1021/ol2027625
Copyright © 2011 American Chemical Society

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    Abstract

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    The first example of enantioselective intermolecular cycloaddition of carbonyl ylides with indoles is described. The cycloaddition of five- and six-membered carbonyl ylides derived from diazodiketoesters with N-methylindoles under catalysis by dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, gave cycloadducts in high yields and with high levels of enantioselectivity (up to 99% ee) as well as excellent exo diastereoselectivity.

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