Phosphine-Catalyzed Domino Annulation of γ-Vinyl Allenoates: Synthesis of Tetrahydrofuro[3,2-]quinoline Derivatives.

Org Lett

State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

Published: May 2024

A novel phosphine-catalyzed domino annulation reaction of γ-vinyl allenoates and -aminotrifluoacetophenones for the construction of terahydrofuro[3,2-]quinoline derivatives has been developed. In this domino reaction, two kinds of terahydrofuro[3,2-]quinoline compounds containing CF groups were obtained with good yields under mild conditions, three new C-N, C-C, and C-O bonds can be built in one step, and the reaction selectivity is achieved by adjusting the reaction conditions. Furthermore, preliminary studies on an asymmetric variant of this reaction proceeded with moderate enantioselectivity.

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http://dx.doi.org/10.1021/acs.orglett.4c00656DOI Listing

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Phosphine-Catalyzed Domino Annulation of γ-Vinyl Allenoates: Synthesis of Tetrahydrofuro[3,2-]quinoline Derivatives.

Org Lett

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State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

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