CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines
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Buchwald_CuH-catalyzed.pdf
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2.35 MB
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Author(s)
Wang, Haoxuan
Yang, Jeffrey
Buchwald, Stephen Leffler
Date Issued
July 2017
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Wang, Haoxuan, et al. “CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines.” Journal of the American Chemical Society, vol. 139, no. 25, June 2017, pp. 8428–31. © 2017 American Chemical Society
Version
Author's final manuscript
Abstract
This report details a general and enantioselective means for the synthesis of alkyl-substituted aziridines. This protocol offers a direct route for the synthesis of alkyl-substituted chiral aziridines from achiral starting materials. Readily accessed allylic hydroxylamine esters undergo copper hydride-catalyzed intramolecular hydroamination with a high degree of regio- and enantiocontrol to afford the aziridine products in good to excellent yields in highly enantioenriched form. The utility of the products derived from this method is further demonstrated through derivatization of the chiral aziridine products to obtain a diverse array of functionalized enantioenriched amines.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
http://dx.doi.org/10.1021/JACS.7B04816
