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Enantioselective Formal Aza-Diels–Alder Reactions of Enones with Cyclic Imines Catalyzed by Primary Aminothioureas

by: Mathieu P. Lalonde, Meredeth A. McGowan, Naomi S. Rajapaksa, Eric N. Jacobsen
J. Am. Chem. Soc. In Journal of the American Chemical Society, Vol. 135, No. 5. (15 January 2013), pp. 1891-1894, doi:10.1021/ja310718f  Key: citeulike:12193112

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Abstract

A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels?Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.


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