Literature DB >> 20577649

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

John P Wolfe1.   

Abstract

Substituted tetrahydrofuran and pyrrolidine moieties are displayed in a wide range of interesting biologically active molecules. The Pd-catalyzed carboetherification or carboamination of γ-hydroxy- and γ-aminoalkenes is a powerful tool for the construction of these heterocycles, as it is convergent and can allow access to a variety of analogs from a single γ-hydroxy- or γ-aminoalkene starting material. This microreview describes the current state of this field.

Entities:  

Year:  2007        PMID: 20577649      PMCID: PMC2890284     

Source DB:  PubMed          Journal:  European J Org Chem        ISSN: 1099-0690


  33 in total

1.  Total synthesis and absolute stereochemistry of plakortone D.

Authors:  Patricia Y Hayes; William Kitching
Journal:  J Am Chem Soc       Date:  2002-08-21       Impact factor: 15.419

2.  Potent inhibitors of the HIV-1 protease incorporating cyclic urea P1-P2 scaffold.

Authors:  Wieslaw M Kazmierski; Eric Furfine; Yolanda Gray-Nunez; Andrew Spaltenstein; Lois Wright
Journal:  Bioorg Med Chem Lett       Date:  2004-11-15       Impact factor: 2.823

3.  Inhibition of cyclin-dependent kinase activity and induction of apoptosis by preussin in human tumor cells.

Authors:  T V Achenbach; E P Slater; H Brummerhop; T Bach; R Müller
Journal:  Antimicrob Agents Chemother       Date:  2000-10       Impact factor: 5.191

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

Authors:  Qifei Yang; Joshua E Ney; John P Wolfe
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

5.  Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction.

Authors:  Joshua E Ney; John P Wolfe
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

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.  Aerobic oxidative amination of unactivated alkenes catalyzed by palladium.

Authors:  Jodie L Brice; Jenna E Harang; Vitaliy I Timokhin; Natia R Anastasi; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

8.  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

9.  Synthesis of polysubstituted tetrahydrofurans via Pd-catalyzed carboetherification reactions.

Authors:  Michael B Hay; John P Wolfe
Journal:  Tetrahedron Lett       Date:  2006-04-17       Impact factor: 2.415

10.  Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation.

Authors:  Kai-Tai Yip; Min Yang; Ka-Lun Law; Nian-Yong Zhu; Dan Yang
Journal:  J Am Chem Soc       Date:  2006-03-15       Impact factor: 15.419

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  49 in total

1.  Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions.

Authors:  Brandon R Rosen; Joshua E Ney; John P Wolfe
Journal:  J Org Chem       Date:  2010-04-16       Impact factor: 4.354

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.  Highly diastereoselective Pd-catalyzed carboetherification reactions of acyclic internal alkenes. Stereoselective synthesis of polysubstituted tetrahydrofurans.

Authors:  Amanda F Ward; John P Wolfe
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

4.  Diastereo- and enantioselective copper-catalyzed intramolecular carboamination of alkenes for the synthesis of hexahydro-1H-benz[f]indoles.

Authors:  Lei Miao; Imranul Haque; Maria R Manzoni; Weng Siong Tham; Sherry R Chemler
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

5.  Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes.

Authors:  Wei Zeng; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

6.  Stereoselective synthesis of substituted 1,3-oxazolidines via Pd-catalyzed carboamination reactions of O-vinyl-1,2-amino alcohols.

Authors:  Amanda F Ward; John P Wolfe
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

7.  Influence of hydroxylamine conformation on stereocontrol in Pd-catalyzed isoxazolidine-forming reactions.

Authors:  Georgia S Lemen; Natalie C Giampietro; Michael B Hay; John P Wolfe
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

8.  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

9.  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

10.  Stereocontrolled Synthesis of Vinyl Boronates and Vinyl Silanes via Atom-Economical Ruthenium-Catalyzed Alkene-Alkyne Coupling.

Authors:  Barry M Trost; Dennis C Koester; Alastair N Herron
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-17       Impact factor: 15.336

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