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A practical electrophilic nitrogen source for the synthesis of chiral primary amines by copper-catalyzed hydroamination

Author(s)
Guo, Sheng; Yang, Jeffrey; Buchwald, Stephen Leffler
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Abstract
A mild and practical method for the catalytic installation of the amino group across alkenes and alkynes has long been recognized as a significant challenge in synthetic chemistry. As the direct hydroamination of olefins using ammonia requires harsh conditions, the development of suitable electrophilic aminating reagents for formal hydroamination methods is of importance. Herein, we describe the use of 1,2-benzisoxazole as a practical electrophilic primary amine source. Using this heterocycle as a new amino group delivery agent, a mild and general protocol for the copper-hydride-catalyzed hydroamination of alkenes and alkynes to form primary amines was developed. This method provides access to a broad range of chiral α-branched primary amines and linear primary amines, as demonstrated by the efficient synthesis of the antiretroviral drug maraviroc and the formal synthesis of several other pharmaceutical agents.
Date issued
2018-10
URI
https://hdl.handle.net/1721.1/126029
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Guo, Sheng, Jeffrey Yang, and Stephen L. Buchwald, "A practical electrophilic nitrogen source for the synthesis of chiral primary amines by copper-catalyzed hydroamination." Journal of the American Chemical Society 140, 46 (Nov. 2018): p. 15976-84 doi 10.1021/JACS.8B10564 ©2018 Author(s)
Version: Author's final manuscript
ISSN
1520-5126

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