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

ABSTRACT: A highly regio- and enantioselective synthesis of 1,2-diamine derivatives from ?-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 ?-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.

SUBMITTER: Ichikawa S 

PROVIDER: S-EPMC6825330 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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

Ichikawa Saki S   Dai Xi-Jie XJ   Buchwald Stephen L SL  

Organic letters 20190517 11

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. ...[more]

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