Organic Letters
Organic Letters
5 years ago

Stereospecific, Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Allylic Pivalates To Deliver Quaternary Stereocenters

Stereospecific, Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Allylic Pivalates To Deliver Quaternary Stereocenters
Javon M. Rabb-Lynch, Kelsey M. Cobb, Mary P. Watson, Alex Manders, Qi Zhou, Megan E. Hoerrner
Recognizing the importance of all-carbon, quaternary stereocenters in complex molecule synthesis, a stereospecific, nickel-catalyzed cross-coupling of allylic pivalates with arylboroxines to deliver products equipped with quaternary stereocenters and internal alkenes was developed. The enantioenriched allylic pivalate starting materials are readily prepared, and a variety of functional groups can be incorporated on both the allylic pivalate and the arylboroxine. Additional advantages include the use of a commercially available and air-stable Ni(II) salt and BISBI ligand, mild reaction conditions, and high yields and ee’s. The observed stereoinversion of this reaction is consistent with an open transition state in the oxidative addition step.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02063

DOI: 10.1021/acs.orglett.7b02063

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