Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination
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nihms-1055824.pdf
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Accepted version
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Author(s)
Ichikawa, Saki
Dai, Xi-Jie
Buchwald, Stephen Leffler
Date Issued
May 2019
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Ichikawa, Saki et al., "Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination." Organic Letters 21, 11 (June 2019): p. 4370–4373 doi. 10.1021/acs.orglett.9b01592 ©2019 Authors
Version
Author's final manuscript
Abstract
A highly regio- and enantioselective synthesis of 1,2-diamine derivatives from γ-substituted allylic pivalamides using copper-catalyzed hydroamination is reported. The N-pivaloyl group is essential, in both facilitating the hydrocupration step and suppressing an unproductive β-elimination from the alkylcopper intermediate. This approach enables an efficient construction of chiral differentially protected vicinal diamines under mild conditions with broad functional group tolerance. ©2019 American Chemical Society.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://dx.doi.org/10.1021/ACS.ORGLETT.9B01592
