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