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Updated: Jun 12, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
A three-step tandem process for the synthesis of bicyclic gamma-lactams
Fiona I McGonagle1, Lindsay Brown, Andrew Cooke
1WestCHEM, Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, UKG12 8QQ.
Abstract:
A one-pot, three-step tandem process has been developed for the direct synthesis of functionalised bicyclic [3.3.0], [4.3.0] and [5.3.0] gamma-lactams from simple allylic trichloroacetimidates. The process involves a palladium(ii) mediated Overman rearrangement followed by the use of Grubbs first generation complex which catalyzes both a ring closing metathesis reaction and a Kharasch cyclization. As well as exploring the scope of this process for the synthesis of a range of functionalised bicyclic gamma-lactams, the use of chiral palladium(ii) catalysts during the Overman rearrangement for the enantioselective synthesis of the bicyclic gamma-lactams is also demonstrated.
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