Alkene-Assisted Nickel-Catalyzed Regioselective 1,4-Addition of Organoboronic Acid to Dienones: A Direct Route to All-Carbon Quaternary Centers

Ya-Chun Hong, Parthasarathy Gandeepan, Subramaniyan Mannathan, Wei-Tse Lee, Chien-Hong Cheng
  • Organic Letters, June 2014, American Chemical Society (ACS)
  • DOI: 10.1021/ol500838h

Formation of All-Carbon Quaternary Centers

What is it about?

A nickel-catalyzed highly regioselective 1,4-addition reaction of boronic acids to dienones to form products with an all-carbon quaternary center is described. The 3-alkenyl group of dienones is the key for the reaction to proceed smoothly. A mechanism involving the coordination of the dienyl group to the nickel center is proposed.

Why is it important?

The reaction is quite interesting that form all carbon quaternary centers via 1,4-addition of bronic acid to dienones. The reaction is driven by the alkene moiety at beta carboon. If no alkene moiety in beta position of enone, no reaction were occurred.

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http://dx.doi.org/10.1021/ol500838h

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