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Urea-Derivative Catalyzed Enantioselective Hydroxyalkylation of Hydroxyindoles with Isatins.

ABSTRACT: The enantioselective transformations of indoles preferentially take place in the more-reactive azole ring. However, the methods for the enantioselective functionalization of the indole benzene ring are scarce. In this paper, a series of bifunctional (thio)urea derivatives were used to organocatalyze the enantioselective Friedel-Crafts hydroxyalkylation of indoles with isatins. The resulting products were obtained in good yields (65-90%) with up to 94% enantiomer excess (ee). The catalyst type and the substrate scope were broadened in this methodology.

SUBMITTER: Wu H

PROVIDER: S-EPMC6864875 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Urea-Derivative Catalyzed Enantioselective Hydroxyalkylation of Hydroxyindoles with Isatins.

Wu Hao H Wang Liming L Zhang Junwei J Jin Ying Y

Molecules (Basel, Switzerland) 20191031 21

The enantioselective transformations of indoles preferentially take place in the more-reactive azole ring. However, the methods for the enantioselective functionalization of the indole benzene ring are scarce. In this paper, a series of bifunctional (thio)urea derivatives were used to organocatalyze the enantioselective Friedel-Crafts hydroxyalkylation of indoles with isatins. The resulting products were obtained in good yields (65-90%) with up to 94% enantiomer excess (ee). The catalyst type an ...[more]

PMID: 31683678

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