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Multicomponent Assembly of Complex Oxindoles by Enantioselective Cooperative Catalysis

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Ternary catalysis enabled the three-component reaction of N-aryl diazoamides, aldehydes, and enamines/indoles, providing access to polyfunctionalized oxindoles in good yields with excellent diastereoselectivities and enantioselectivities (>90 examples, up to 94 % yield, 99 % ee, and >20 : 1 dr). The reaction involves the assembly of two highly reactive intermediates generated in situ by orthogonal catalytic processes under mild and operationally simple reaction conditions.


Abstract

Chiral oxindoles are important chemical scaffolds found in many natural products, and their enantioselective synthesis thus attracts considerable attention. Highly diastereo- and enantioselective synthetic methods for constructing C3 quaternary oxindoles have been well-developed. However, the efficient synthesis of chiral 3-substituted tertiary oxindoles has been rarely reported due to the ease of racemization of the tertiary stereocenter via enolization. Therefore, we herein report on the multicomponent assembly (from N-aryl diazoamides, aldehydes, and enamines/indoles) of complex oxindoles by enantioselective cooperative catalysis. These reactions proceed under mild conditions and show broad substrate scope, affording the desired coupling products (>90 examples) with good to excellent stereocontrol. Additionally, this research also demonstrates the synthetic potential of this annulation by constructing the 6,6,5-tricyclic lactone core structure of Speradine A.

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