Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination

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 a...

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Bibliographic Details
Main Authors: Ichikawa, Saki (Author), Dai, Xi-Jie (Author), Buchwald, Stephen Leffler (Author)
Other Authors: Massachusetts Institute of Technology. Department of Chemistry (Contributor)
Format: Article
Language:English
Published: American Chemical Society (ACS), 2020-06-29T13:28:45Z.
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100 1 0 |a Ichikawa, Saki  |e author 
100 1 0 |a Massachusetts Institute of Technology. Department of Chemistry  |e contributor 
700 1 0 |a Dai, Xi-Jie  |e author 
700 1 0 |a Buchwald, Stephen Leffler  |e author 
245 0 0 |a Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination 
260 |b American Chemical Society (ACS),   |c 2020-06-29T13:28:45Z. 
856 |z Get fulltext  |u https://hdl.handle.net/1721.1/126008 
520 |a 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. 
520 |a National Institute of Health (R35-GM122483) 
520 |a National Institute of Health (R01-GM58160) 
520 |a NIH (Grant no. GM58160-17S1) 
546 |a en 
655 7 |a Article 
773 |t Organic Letters