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Remarkable [3+2] Annulations of Electron-Rich Olefins with Unstabilized Azomethine Ylides

Jennifer E. Davoren*, David L. Gray*, Anthony R. Harris, Deane M. Nason, Wenjian Xu

*Neurosciences Chemistry, Pfizer Global Research and Development, Eastern Point Road, Groton, CT 06340, USA, Email:

J. E. Davoren, D. L. Gray, A. R. Harris, D. M. Nason, W. Xu, Synlett, 2010, 2490-2492.

DOI: 10.1055/s-0030-1258026


An unstabilized azomethine ylide generated from commercial trimethylamine N-oxide undergoes a remarkable 1,3-dipolar cycloaddition with electron-rich and unpolarized olefins to give challenging 3,4-di­substituted pyrrolidines in good yield. A broad range of substituents on the alkenes are tolerated provided they are compatible with excess LDA.

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Key Words

3,4-disubstituted pyrrolidine, 1,3-dipolar cycloaddition, unstabilized azomethine ylide

ID: J60-Y2010-2790