Asymmetric Palladium-Catalyzed Carboamination Reactions for the Synthesis of Enantiomerically Enriched 2-(Arylmethyl)- and 2-(Alkenylmethyl)pyrrolidines
- 18 August 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (35), 12157-12159
- https://doi.org/10.1021/ja106989h
Abstract
The enantioselective synthesis of 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidine derivatives via Pd-catalyzed alkene carboamination reactions is described. These transformations generate enantiomerically enriched products with up to 94% ee from readily available alkenyl or aryl bromides and N-boc-pent-4-enylamines. The application of this method to a concise asymmetric synthesis of (−)-tylophorine is also discussed.Keywords
This publication has 38 references indexed in Scilit:
- Highly Enantioselective Intramolecular Cyanoamidation: (+)-Horsfiline, (−)-Coerulescine, and (−)-EsermetholeOrganic Letters, 2010
- Mild Conditions for Pd-Catalyzed Carboamination of N-Protected Hex-4-enylamines and 1-, 3-, and 4-Substituted Pent-4-enylamines. Scope, Limitations, and Mechanism of Pyrrolidine FormationThe Journal of Organic Chemistry, 2008
- Total Synthesis of (S)-(+)-Tylophorine Via Enantioselective Intramolecular Alkene CarboaminationThe Journal of Organic Chemistry, 2008
- Enantioselective Synthesis of 3,3-Disubstituted Oxindoles through Pd-Catalyzed CyanoamidationOrganic Letters, 2008
- A Chiral Phosphoramidite beyond Monodentate Coordination: Secondary π-Interactions Turn a Dangling Aryl into a Two-, Four-, or Six-Electron Donor in d6 and d8 ComplexesOrganometallics, 2008
- Chiral N-Heterocyclic Carbene−Pd(0)-Catalyzed Asymmetric Diamination of Conjugated Dienes and TrieneThe Journal of Organic Chemistry, 2007
- Copper(II)-Catalyzed Enantioselective Intramolecular Carboamination of AlkenesJournal of the American Chemical Society, 2007
- Palladium-Catalyzed Asymmetric [3+2] Cycloaddition of Trimethylenemethane with IminesJournal of the American Chemical Society, 2007
- Palladium‐Catalyzed Carboetherification and Carboamination Reactions of γ‐Hydroxy‐ and γ‐Aminoalkenes for the Synthesis of Tetrahydrofurans and PyrrolidinesEuropean Journal of Organic Chemistry, 2007
- A Concise Stereoselective Synthesis of Preussin, 3-epi-Preussin, and AnaloguesOrganic Letters, 2006