Diastereoselective and Enantioselective Intramolecular Amino−Zinc−Enolate Carbometalation Reactions. A New Polysubstituted Pyrrolidines Synthesis
- 21 March 1998
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 63 (8), 2442-2450
- https://doi.org/10.1021/jo970813e
Abstract
The amino−zinc−enolate cyclization allowed a new and straightforward route to polysubstituted pyrrolidines from simple starting materials. From this study, we have been able to determine, for the first time, the stereochemical influence of the substituents on the ring in the carbocyclization reaction. The diastereoselectivity thus obtained was explained by a chairlike amino−zinc−enolate transition state.Keywords
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