Asymmetric (CpRh)-Rh-x(III)-Catalyzed Acrylic Acid C-H Functionalization with Allenes Provides Chiral gamma-Lactones

A chiral cyclopentadienyl (Cp-x) ligand featuring the semi-saturated H8-binaphthyl backbone as the chiral element was developed. Its application potential was demonstrated by (CpRhIII)-Rh-x-catalyzed C-H bond functionalization of acryl acids and allenes, exhibiting superior catalytic performance compared to other Cp-x ligands. The outlined enantioselective [4 + 1]-annulation process results in synthetically attractive alpha, beta-unsaturated gamma-lactones having an allylic stereogenic center, which were obtained in enantioselectivities of up to 99:1 enantiomeric ratio.


Published in:
Acs Catalysis, 10, 15, 8231-8236
Year:
Aug 07 2020
Publisher:
Washington, AMER CHEMICAL SOC
ISSN:
2155-5435
Keywords:




 Record created 2020-09-10, last modified 2020-10-29


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