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Stereoselective synthesis of C3-tetrasubstituted oxindoles via copper catalyzed asymmetric propargylation† † Electronic supplementary information (ESI) available. CCDC 2181911 and 2181912. For ESI and crystallographic data in CIF or other electronic format see https://doi.org/10.1039/d2ra04603b

ABSTRACT: Herein, a copper catalyzed asymmetric propargylation of 2-oxindole-3-carboxylate esters with terminal propargylic esters is described. This strategy successfully provides a direct approach to constructing a broad range of chiral C3-tetrasubstituted oxindoles with contiguous tertiary and quaternary carbon stereocenters in high yields and excellent enantioselectivities (16 examples, up to 99% yield and 98% ee). Moreover, the diastereoisomers of the two newly formed stereocenters can be separated by silica gel chromatography, thereby providing a valuable stereoselective access to all four possible stereoisomers of C3-tetrasubstituted oxindoles. Herein, a copper catalyzed asymmetric propargylation of 2-oxindole-3-carboxylate esters with terminal propargylic esters is described.

SUBMITTER: Wang J

PROVIDER: S-EPMC9490778 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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