Enantioselective Synthesis of Dispirooxindole Derivatives via Asymmetric Catalytic Cascade Reactions

Dedicated to Prof. Guo-Qiang Lin for his 80^th birthday.

Abstract

A series of optically active 3,3′-pyrrolidinyl-dispirooxindole derivatives containing a CF₃ moiety have been efficiently constructed through asymmetric catalytic cascade reactions catalyzed by cinchona-derived bifunctional squaramide catalyst, bearing four contiguous stereogenic centers, two of which are vicinal spiro-stereocenters. Additionally, a wide range of substituted products were achieved with moderate to high yields (up to 99% yield) and excellent stereoselectivities (up to >20:1 dr for all cases and up to 99% ee).

Key words

organocatalysis - dispirooxindole - cascade reactions - four contiguous stereogenic centers - new substrates

Publikationsverlauf

Eingereicht: 16. Dezember 2022

Angenommen nach Revision: 22. Januar 2023

Accepted Manuscript online:
22. Januar 2023

Artikel online veröffentlicht:
27. Februar 2023

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