Disulfonimide catalyzed asymmetric intramolecular hydroamination of alkenyl thioureas: Concentration effect in the hydroamination

Disulfonimide catalyzed asymmetric intramolecular hydroamination of alkenyl thioureas: Concentration effect in the hydroamination

Disulfonimide (DSI)-catalyzed asymmetric intramolecular hydroamination of alkenyl thiourea was examined. The reaction proceeded even under dilute concentrations and high temperatures, and the hydroamination product was obtained with good chemical yield and moderate enantioselectivity. The density fu...

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Bibliographic Details
Published in:Tetrahedron Vol. 94; p. 132332
Main Authors: Takagi, Ryukichi, Duong, Duyen Thi, Ichiki, Toshiya
Format: Journal Article
Language:English
Published: Elsevier Ltd 13-08-2021
Subjects:
Asymmetric reaction
Disulfonimide
Hydroamination
Hydrogen bond
Thiourea
Thiourea
Hydroamination
Asymmetric reaction
Disulfonimide
Hydrogen bond
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Summary:Disulfonimide (DSI)-catalyzed asymmetric intramolecular hydroamination of alkenyl thiourea was examined. The reaction proceeded even under dilute concentrations and high temperatures, and the hydroamination product was obtained with good chemical yield and moderate enantioselectivity. The density functional theory (DFT) calculations on the reaction supported the mechanism in which the thiourea moiety of the alkenyl amine acted as a dual hydrogen bond donor. [Display omitted] •Disulfonimide-catalyzed asymmetric intramolecular hydroamination of alkenyl thiourea was examined.•The hydroamination product was obtained with good chemical yield and moderate enantioselectivity.•The reaction proceeded under dilute without stirring.•The mechanism, in which the thiourea moiety acted as a hydrogen bond donor, was proposed.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2021.132332