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

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

Organic Letters,
2014, 16, (11), 3036-3039; 10.1021/ol5011505


The Davies group report a novel synthesis of beta-lactones via a dirhodium-catalyzed intramolecular C–H insertion.

The incorporation of a halo- or trifluoromethyl-substitutent at the ortho position on the aryl group of a donor/acceptor carbene effectively shuts down many of the deleterious intermolecular side reactions normally associated with these systems, enabling the intramolecular reaction profile.

Beta-lactones are structural motifs of significant pharmaceutical interest due to their biological activity and this represents a streamlined entry into these valuable molecules.

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