Regio‐ and enantioselective nickel-alkyl catalyzed hydroalkylation of alkynes

Regio‐ and enantioselective nickel-alkyl catalyzed hydroalkylation of alkynes

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Abstract The migratory insertion of metal-hydride into alkene has allowed regioselective access to organometallics, readily participating in subsequent functionalization as one conventional pathway of hydroalkylation, whereas analogous process Gastrointestinal - Probiotics with feedstock alkyne is drastically less explored.Among few examples, the regioselectivity of metal-hydride insertion is mostly governed by electronic bias of alkynes.To alter the regioselectivity and drastically expand the intermediate pools that we can access, one aspirational design is through alternative nickel-alkyl insertion, providing opposite regioselectivity induced by steric GF COCONUT SHRED UNSWT demand.Leveraging in situ formed nickel-alkyl species, we herein report the regio- and enantioselective hydroalkylation of alkynes with broad functional group tolerance, excellent regio- and enantioselectivity, enabling efficient route to diverse valuable chiral allylic amines motifs.Preliminary mechanistic studies indicate the aminoalkyl radical species can participate in metal-capture and lead to formation of nickel-alkyl, of which the migratory insertion is key to reverse regioselectivity observed in metal-hydride insertion.