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Updated: Jun 20, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Asymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/N-heterocyclic carbene
Stephen P Lathrop1, Tomislav Rovis
1Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Abstract:
A one-pot, asymmetric multicatalytic formal [3+2] reaction between 1,3-dicarbonyls and alpha,beta-unsaturated aldehydes is described. The multicatalytic process involves a secondary amine catalyzed Michael addition followed by a N-heterocyclic carbene catalyzed intramolecular crossed benzoin reaction to afford densely functionalized cyclopentanones with high enantioselectivities. The reaction proceeds with a variety of alkyl and aryl enals as well as a range of 1,3-dicarbonyls (diketones and beta-ketoesters). The functionalized products are obtained from cheap, readily available starting materials in a rapid and efficient manner in a one-pot, one-step operation.
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