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Publication 69  

  1. Ni-Catalyzed Regiodivergent and Stereoselective Hydroalkylation of Acyclic Branched Dienes with Unstabilized C(sp3) Nucleophiles
    Wen Shao, Céline Besnard, Laure Guénée, Clément Mazet*
    J. Am. Chem. Soc. 2020, 142, 16486-16492

Two complementary regiodivergent [(P,N)Ni]-catalyzed hydroalkylations of branched dienes are reported. When amides are employed as unstabilized C(sp3) nucleophiles, a highly regioselective 1,4-addition process is favored. The addition products are obtained in high yield and with excellent stereocontrol of the internal olefin. Using a chiral ligand and imides as carbon nucleophiles, a 3,4-addition protocol was developed enabling to construct two contiguous tertiary stereocenters in a single step with moderate to high levels of diastereocontrol and excellent enantiocontrol. Both methods operate under mild reaction conditions, display broad scope and excellent functional group tolerance. The synthetic potential of the 3,4-hydroalkylation reaction was established via a series of post-catalytic modifications.

open archive unige:141221

Editor’s version DOI: 10.1021/jacs.0c08319 

AAM DOI: 10.26037/yareta:yalv5wsmofcrtkakagppuw4ydy 

Dataset DOI: 10.26037/yareta:btrsg422lbfmhmw34md6f4hhzm