Synfacts 2019; 15(12): 1403
DOI: 10.1055/s-0039-1691118
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

1,3-Diene Difunctionalization: Copper-Catalyzed 1,2-Amino Oxygenation

Contributor(s):
Mark Lautens
,
Egor M. Larin
Hemric BN, Chen AW, Wang Q. * Duke University, Durham, USA
Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio- and Site-Selective Three-Component Reaction with O-Acylhydroxylamines and Carboxylic Acids.

ACS Catal. 2019;
9: 10070-10076
Further Information

Publication History

Publication Date:
18 November 2019 (online)

 

Significance

Diene difunctionalization via selective installation of two heteroatoms is an underdeveloped field, albeit one that could generate molecular complexity quickly and efficiently. Challenges of regio- and siteselectivity are inherent in this strategy.


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Comment

The authors report a copper-catalyzed three-component method to achieve diene difunctionalization. The approach uses O-acyl hydroxylamines as electrophilic sources of nitrogen, and carboxylic acids as nucleophilic sources of oxygen to facilitate a 1,2-amino oxygenation of the least substituted end of the 1,3-dienes. The reaction is highly selective for dienes, even over other olefin moieties.


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