Literature DB >> 15957894

Palladium-catalyzed tandem N-arylation/carboamination reactions for the stereoselective synthesis of N-aryl-2-benzyl pyrrolidines.

Qifei Yang1, Joshua E Ney, John P Wolfe.   

Abstract

[reaction: see text] The tandem N-arylation/carboamination of gamma-amino alkenes with two different aryl bromides provides rapid entry to differentially arylated N-aryl-2-benzyl pyrrolidine derivatives in good yields with good to excellent levels of diastereoselectivity. The selective diarylation is achieved in a one-pot process by an in situ modification of the palladium catalyst via phosphine ligand exchange.

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Year:  2005        PMID： 15957894      PMCID： PMC2750836          DOI： 10.1021/ol050647u

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  15 in total

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2.  Tandem Reactions in Organic Synthesis: Novel Strategies for Natural Product Elaboration and the Development of New Synthetic Methodology.

Authors:  Philip J. Parsons; Clive S. Penkett; Adrian J. Shell
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3.  Tandem catalysis: the sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes.

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4.  Tandem reactions, cascade sequences, and biomimetic strategies in total synthesis.

Authors:  K C Nicolaou; Tamsyn Montagnon; Scott A Snyder
Journal:  Chem Commun (Camb)       Date:  2003-03-07       Impact factor: 6.222

5.  Two birds with one metallic stone: single-pot catalysis of fundamentally different transformations.

Authors:  Alain Ajamian; James L Gleason
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-19       Impact factor: 15.336

6.  Palladium-catalyzed synthesis of N-aryl-2-benzylindolines via tandem arylation of 2-allylaniline: control of selectivity through in situ catalyst modification.

Authors:  Ricardo Lira; John P Wolfe
Journal:  J Am Chem Soc       Date:  2004-11-03       Impact factor: 15.419

7.  Palladium-catalyzed synthesis of N-aryl pyrrolidines from gamma-(N-Arylamino) alkenes: evidence for chemoselective alkene insertion into Pd--N bonds.

Authors:  Joshua E Ney; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-05       Impact factor: 15.336

8.  Stereospecific synthesis of highly substituted skipped dienes through multifunctional palladium catalysis.

Authors:  Avinash N Thadani; Viresh H Rawal
Journal:  Org Lett       Date:  2002-11-28       Impact factor: 6.005

9.  Stereoselective synthesis of tetrahydrofurans via the palladium-catalyzed reaction of aryl bromides with gamma-hydroxy alkenes: evidence for an unusual intramolecular olefin insertion into a Pd(Ar)(OR) intermediate.

Authors:  John P Wolfe; Michael A Rossi
Journal:  J Am Chem Soc       Date:  2004-02-18       Impact factor: 15.419

10.  Ruthenium-catalyzed one-pot double allylation/cycloisomerization of 1,3-dicarbonyl compounds leading to exo-methylenecyclopentanes.

Authors:  Yoshihiko Yamamoto; Yu-ichiro Nakagai; Kenji Itoh
Journal:  Chemistry       Date:  2004-01-05       Impact factor: 5.236
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  21 in total

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2.  Palladium-catalyzed alkene carboamination reactions for the synthesis of substituted piperazines.

Authors:  Josephine S Nakhla; Danielle M Schultz; John P Wolfe
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

3.  Palladium-catalyzed synthesis of 2,1'-disubstituted tetrahydrofurans from gamma-hydroxy internal alkenes. Evidence for alkene insertion into a Pd-O bond and stereochemical scrambling via beta-hydride elimination.

Authors:  Michael B Hay; John P Wolfe
Journal:  J Am Chem Soc       Date:  2005-11-30       Impact factor: 15.419

4.  A concise stereoselective synthesis of Preussin, 3-epi-Preussin, and analogues.

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Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

5.  A multiligand based Pd catalyst for C-N cross-coupling reactions.

Authors:  Brett P Fors; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-27       Impact factor: 15.419

6.  A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas.

Authors:  Jonathan A Fritz; Josephine S Nakhla; John P Wolfe
Journal:  Org Lett       Date:  2006-06-08       Impact factor: 6.005

7.  Two palladium-catalyzed domino reactions from one set of substrates/reagents: efficient synthesis of substituted indenes and cis-stilbenoid hydrocarbons from the same internal alkynes and hindered Grignard reagents.

Authors:  Cheng-Guo Dong; Pik Yeung; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

8.  Palladium-Catalyzed Carboetherification and Carboamination Reactions of γ-Hydroxy- and γ-Aminoalkenes for the Synthesis of Tetrahydrofurans and Pyrrolidines.

Authors:  John P Wolfe
Journal:  European J Org Chem       Date:  2007-02

9.  Recent Developments in Pd-Catalyzed Alkene Aminoarylation Reactions for the Synthesis of Nitrogen Heterocycles.

Authors:  Danielle M Schultz; John P Wolfe
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

10.  Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.

Authors:  John P Wolfe
Journal:  Synlett       Date:  2006-11-13       Impact factor: 2.454
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