A Concise Asymmetric Synthesis of cis-2,6-Disubstituted N-Aryl Piperazines via Pd-Catalyzed Carboamination Reactions
- 25 July 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (17) , 3279-3282
- https://doi.org/10.1021/ol071241f
Abstract
A concise, modular, asymmetric synthesis of cis-2,6-disubstituted piperazines from readily available amino acid precursors is described. The key step in the synthesis is a Pd-catalyzed carboamination of a N1-aryl-N2-allyl-1,2-diamine with an aryl bromide. The products are obtained in 14−20:1 dr, with >97% ee, and the key cyclizations are the first examples of six-membered ring formation via Pd-catalyzed carboamination reactions of unsaturated amines with aryl halides.Keywords
This publication has 27 references indexed in Scilit:
- Pyrrolidine and Piperidine Formation via Copper(II) Carboxylate-Promoted Intramolecular Carboamination of Unactivated Olefins: Diastereoselectivity and MechanismThe Journal of Organic Chemistry, 2007
- Mild Conditions for the Synthesis of Functionalized Pyrrolidines via Pd-Catalyzed Carboamination ReactionsOrganic Letters, 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
- Synthesis of N‐Aryl‐2‐allylpyrrolidines via Palladium‐Catalyzed Carboamination Reactions of γ‐(N‐Arylamino)alkenes with Vinyl BromidesAdvanced Synthesis & Catalysis, 2005
- Selective Synthesis of 5- or 6-Aryl Octahydrocyclopenta[b]pyrroles from a Common Precursor through Control of Competing Pathways in a Pd-Catalyzed ReactionJournal of the American Chemical Society, 2005
- Palladium-Catalyzed Synthesis of N-Aryl-2-benzylindolines via Tandem Arylation of 2-Allylaniline: Control of Selectivity through in Situ Catalyst ModificationJournal of the American Chemical Society, 2004
- Palladium‐Catalyzed Synthesis of N‐Aryl Pyrrolidines from γ‐(N‐Arylamino) Alkenes: Evidence for Chemoselective Alkene Insertion into Pd-N BondsAngewandte Chemie International Edition in English, 2004
- The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged SubstructuresChemical Reviews, 2003
- .beta.-Migratory insertion reactions of (.eta.5-C5R'5)Rh(L)(C2H4)R+BF4- (R' = hydrogen, methyl; R = hydrogen, ethyl; L = P(OMe)3, PMe3). Comparison of the energetics of hydride versus alkyl migrationJournal of the American Chemical Society, 1992