Ir‐Catalyzed Enantioselective Intra‐ and Intermolecular Formal C−H Conjugate Addition to β‐Substituted α,β‐Unsaturated Esters

Takanori Shibata, Hisaki Kurita, Sahoko Onoda, Kyalo Stephen Kanyiva

Asian Journal of Organic Chemistry · 2018 · 43 citations · 45 references

Concepts

Abstract

Abstract An enantioselective intramolecular formal C−H conjugate addition of 4‐methyl 1‐aryl 2‐methylfumarates proceeded using a chiral iridium catalyst. A benzoylamide group served as a directing group, and chiral γ‐lactones with a quaternary all‐carbon stereogenic center were obtained with up to excellent ee . In the intermolecular reaction of N ‐arylbenzamides with β‐substituted acrylates, C−H bond activation selectively occurred at the ortho ‐position of carbonyl groups, and highly enantioselective formal C−H conjugate addition proceeded.

References

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