Literature DB >> 17650007

A concise asymmetric synthesis of cis-2,6-disubstituted N-aryl piperazines via Pd-catalyzed carboamination reactions.

Josephine S Nakhla1, John P Wolfe.   

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.

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Year:  2007        PMID： 17650007      PMCID： PMC2730114          DOI： 10.1021/ol071241f

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


  20 in total

1.  Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions.

Authors:  Myra Beaudoin Bertrand; Matthew L Leathen; John P Wolfe
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

2.  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

3.  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

4.  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

5.  Diastereoselective synthesis of piperazines by manganese-mediated reductive cyclization.

Authors:  Gregory J Mercer; Matthew S Sigman
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

6.  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

7.  Palladium-catalyzed highly stereoselective synthesis of N-aryl-3-arylmethylisoxazolidines via tandem arylation of O-homoallylhydroxylamines.

Authors:  Jinsong Peng; Wenqing Lin; Shixue Yuan; Yuanwei Chen
Journal:  J Org Chem       Date:  2007-03-17       Impact factor: 4.354

8.  Copper(II) acetate promoted oxidative cyclization of arylsulfonyl-o-allylanilines.

Authors:  Eric S Sherman; Sherry R Chemler; Tai Boon Tan; Oksana Gerlits
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005

9.  Synthesis of highly substituted enantiopure piperazines and ketopiperazines from vicinal N-sulfinyl diamines.

Authors:  Alma Viso; Roberto Fernández de la Pradilla; Aida Flores; Ana García; Mariola Tortosa; María L López-Rodríguez
Journal:  J Org Chem       Date:  2006-02-17       Impact factor: 4.354

10.  Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: diastereoselectivity and mechanism.

Authors:  Eric S Sherman; Peter H Fuller; Dhanalakshmi Kasi; Sherry R Chemler
Journal:  J Org Chem       Date:  2007-04-12       Impact factor: 4.354
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  16 in total

1.  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

2.  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

3.  Asymmetric total synthesis of (+)-merobatzelladine B.

Authors:  Nicholas R Babij; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-16       Impact factor: 15.336

4.  Enantioselective synthesis of α-secondary and α-tertiary piperazin-2-ones and piperazines by catalytic asymmetric allylic alkylation.

Authors:  Katerina M Korch; Christian Eidamshaus; Douglas C Behenna; Sangkil Nam; David Horne; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-07       Impact factor: 15.336

5.  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

6.  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

7.  New strategy for the synthesis of substituted morpholines.

Authors:  Matthew L Leathen; Brandon R Rosen; John P Wolfe
Journal:  J Org Chem       Date:  2009-07-17       Impact factor: 4.354

8.  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 formation.

Authors:  Myra Beaudoin Bertrand; Joshua D Neukom; John P Wolfe
Journal:  J Org Chem       Date:  2008-10-23       Impact factor: 4.354

9.  Stereoselective synthesis of imidazolidin-2-ones via Pd-catalyzed alkene carboamination. Scope and limitations.

Authors:  Jonathan A Fritz; John P Wolfe
Journal:  Tetrahedron       Date:  2008       Impact factor: 2.457

10.  Copper(II) carboxylate-promoted intramolecular carboamination of alkenes for the synthesis of polycyclic lactams.

Authors:  Peter H Fuller; Sherry R Chemler
Journal:  Org Lett       Date:  2007-11-29       Impact factor: 6.005
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