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

…, MA McGowan, NS Rajapaksa…

Index: Lalonde, Mathieu P.; McGowan, Meredeth A.; Rajapaksa, Naomi S.; Jacobsen, Eric N. Journal of the American Chemical Society, 2013 , vol. 135, # 5 p. 1891 - 1894

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Citation Number: 65

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.