253. Role of Ortho-Substituents on Rhodium-Catalyzed Asymmetric Synthesis of β-Lactones by Intramolecular C–H Insertions of Aryldiazoacetates

Authors: Liangbing Fu, Hengbin Wang, and Huw M. L. Davies

Org. Lett.,

2014, 16 (11), pp 3036–3039.


A rhodium-catalyzed asymmetric synthesis of β-lactones via intramolecular C–H insertion into the ester group of aryldiazoacetates has been developed. The β-lactones were synthesized in high yields and with high levels of diastereo- and enantioselectivity. Halo and trifluoromethyl substituents at the ortho position of the aryldiazoacetates enhance intramolecular C–H insertions over intermolecular reactions, allowing C–H insertion of even methyl C–H bonds.

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