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. 2016 Jan 27;138(3):742-5.
doi: 10.1021/jacs.5b11441. Epub 2016 Jan 15.

Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts

Chunlin Wu  1 , Guizhou Yue  2 , Christian Duc-Trieu Nielsen  1 , Kai Xu  1 , Hajime Hirao  1 , Jianrong Steve Zhou  1
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Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts

Chunlin Wu et al. J Am Chem Soc. .

Abstract

Copper complexes of phosphoramidites efficiently catalyzed asymmetric addition of arylboron reagents to acyclic enones. Importantly, rare 1,4-insertion of arylcopper(I) was identified which led directly to O-bound copper enolates. The new mechanism is fundamentally different from classical oxidative addition/reductive elimination of organocopper(I) on enones.

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