A practical electrophilic nitrogen source for the synthesis of chiral primary amines by copper-catalyzed hydroamination
Name
nihms-1014712.pdf
Description
Accepted version
Size
1.48 MB
Format
Adobe PDF
Checksum (MD5)
e08e64d96ffc8aff2bc41f99e99785a2
Author(s)
Guo, Sheng
Yang, Jeffrey
Buchwald, Stephen Leffler
Date Issued
October 2018
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
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/JACS.8B10564
