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Issue 6, 2020
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A Co(ii)-catalyzed asymmetric ring opening reaction of spiro-epoxyoxindoles with allylboron

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Abstract

Stereoconvergent reactions of epoxides are challenging and very limited. Herein, we report the first stereoconvergent ring opening allylation of epoxides, which was catalysed by a Co(II)/bisoxazoline catalyst, to realize the reaction between spiroepoxyoxindoles and potassium allyltrifluoroborate. This catalytic system can tolerate a wide range of spiroepoxyoxindoles. The desired chiral oxindoles bearing quaternary stereocenters could be prepared with yields of 64–90% and enantioselectivities of 57–78%. A gram-scale reaction showed the practical applicability of this enantioselective catalysis. Furthermore, preliminary mechanistic studies indicate that this reaction proceeds via a sequential epoxide-ring-opening and enantioselective addition process.

Graphical abstract: A Co(ii)-catalyzed asymmetric ring opening reaction of spiro-epoxyoxindoles with allylboron

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Article information


Submitted
16 Jan 2020
Accepted
16 Feb 2020
First published
18 Feb 2020

Org. Chem. Front., 2020,7, 862-867
Article type
Research Article

A Co(II)-catalyzed asymmetric ring opening reaction of spiro-epoxyoxindoles with allylboron

L. Wu, Q. Shao, L. Kong, J. Chen, Q. Wei and W. Zhang, Org. Chem. Front., 2020, 7, 862
DOI: 10.1039/D0QO00072H

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