Journal
ACS CATALYSIS
Volume 13, Issue 1, Pages 141-146Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c05874
Keywords
Allylation; Acylation; Cooperative Catalysis; Aldehyde; Nickel
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We developed a highly enantioselective acyl C-H allylation reaction, which can synthesize highly enantioselective α-stereogenic β,γ-unsaturated 1,4-dicarbonyl compounds.
Herein, we developed a highly enantioselective acyl C-H allylation of aldehydes and formamides, which proceeds under the cooperative catalysis of a chiral PHOX nickel complex and tetrabutylammonium decatungstate (TBADT). With readily available Morita-Baylis-Hillman adducts as the electrophilic allylating agent, the reported reaction allows for the synthesis of alpha-stereogenic beta,gamma-unsaturated 1,4-dicarbonyl compounds in a highly enantioselective manner. The preliminary mechanistic investigations point to an enantioconvergent reaction pathway, in which rapid kinetic resolution of the starting allyl acetates through oxidative addition to Ni(0) is followed by dynamic kinetic resolution of the resultant allyl Ni(II) complexes via the interaction with acyl radicals generated by TBADT-mediated homolytic acyl C-H bond cleavage.
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