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Issue 31, 2019
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Highly enantioselective addition of sulfur-containing heterocycles to isatin-derived ketimines

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Abstract

In this study, we report a highly stereoselective addition of sulfur-containing heterocyclic compounds to isatin-derived ketimines efficiently catalyzed by cinchonidine-derived bifunctional tertiary aminothiourea (1 mol%). This organocatalytic methodology furnishes a new type of optically active heterocyclic compound with two adjacent chiral quaternary carbon stereocenters in good yield (up to 98%), with excellent diastereoselectivity (up to 20 : 1 dr) and high enantioselectivity (up to 95% ee).

Graphical abstract: Highly enantioselective addition of sulfur-containing heterocycles to isatin-derived ketimines

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Supplementary files

Article information


Submitted
12 Jun 2019
Accepted
10 Jul 2019
First published
25 Jul 2019

Org. Biomol. Chem., 2019,17, 7309-7314
Article type
Communication

Highly enantioselective addition of sulfur-containing heterocycles to isatin-derived ketimines

M. Franc, M. Urban, I. Císařová and J. Veselý, Org. Biomol. Chem., 2019, 17, 7309
DOI: 10.1039/C9OB01338E

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