Literature DB >> 26313846

Asymmetric Pd-Catalyzed Alkene Carboamination Reactions for the Synthesis of 2-Aminoindane Derivatives.

Derick R White1, Johnathon T Hutt1, John P Wolfe1.   

Abstract

A new type of Pd-catalyzed alkene carboamination reaction that provides direct access to enantioenriched 2-aminoindanes from 2-allylphenyltriflate derivatives and aliphatic amines is described. A catalyst generated in situ from Pd(OAc)2 and (S)-tert-butylPHOX provides the functionalized carbocycles in good yield with up to >99:1 er. The transformations occur via a key anti-aminopalladation that involves intermolecular attack of an amine nucleophile on an arylpalladium alkene complex.

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Year:  2015        PMID: 26313846      PMCID: PMC4934887          DOI: 10.1021/jacs.5b07203

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  14 in total

1.  The enantioselective Tsuji allylation.

Authors:  Douglas C Behenna; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

2.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

3.  Catalytic asymmetric synthesis of sterically hindered tertiary α-aryl ketones.

Authors:  Robert Doran; Patrick J Guiry
Journal:  J Org Chem       Date:  2014-09-18       Impact factor: 4.354

4.  Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric palladium-catalyzed alkene carboamination reactions.

Authors:  Brett A Hopkins; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-31       Impact factor: 15.336

5.  Enantioselective Synthesis of Tetrahydroquinolines, Tetrahydroquinoxalines, and Tetrahydroisoquinolines via Pd-Catalyzed Alkene Carboamination Reactions.

Authors:  B A Hopkins; J P Wolfe
Journal:  Chem Sci       Date:  2014-12-01       Impact factor: 9.825

6.  Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives.

Authors:  Linda D Simmler; Anna Rickli; York Schramm; Marius C Hoener; Matthias E Liechti
Journal:  Biochem Pharmacol       Date:  2014-01-28       Impact factor: 5.858

7.  Asymmetric palladium-catalyzed carboamination reactions for the synthesis of enantiomerically enriched 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidines.

Authors:  Duy N Mai; John P Wolfe
Journal:  J Am Chem Soc       Date:  2010-09-08       Impact factor: 15.419

Review 8.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Catalytic enantioselective Meerwein-Eschenmoser Claisen rearrangement: asymmetric synthesis of allyl oxindoles.

Authors:  Elizabeth C Linton; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

10.  Influence of catalyst structure and reaction conditions on anti- versus syn-aminopalladation pathways in Pd-catalyzed alkene carboamination reactions of N-allylsulfamides.

Authors:  Ryan M Fornwald; Jonathan A Fritz; John P Wolfe
Journal:  Chemistry       Date:  2014-06-17       Impact factor: 5.236

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  13 in total

1.  Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction.

Authors:  Jamie R Allen; Ana Bahamonde; Yukino Furukawa; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2019-05-24       Impact factor: 15.419

2.  Enantioselective Markovnikov Addition of Carbamates to Allylic Alcohols for the Construction of α-Secondary and α-Tertiary Amines.

Authors:  Ana Bahamonde; Buthainah Al Rifaie; Victor Martín-Heras; Jamie R Allen; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2019-05-24       Impact factor: 15.419

3.  Pd-Catalyzed Alkene Difunctionalization Reactions of Malonate Nucleophiles: Synthesis of Substituted Cyclopentanes via Alkene Aryl-Alkylation and Akenyl-Alkylation.

Authors:  Derick R White; Elsa M Hinds; Evan C Bornowski; John P Wolfe
Journal:  Org Lett       Date:  2019-04-25       Impact factor: 6.005

4.  Recent Developments in Pd(0)-Catalyzed Alkene Carboheterofunctionalization Reactions.

Authors:  Zachary J Garlets; Derick R White; John P Wolfe
Journal:  Asian J Org Chem       Date:  2017-03-10       Impact factor: 3.319

5.  Cu-Catalyzed Three-Component Carboamination of Alkenes.

Authors:  Samuel N Gockel; Travis L Buchanan; Kami L Hull
Journal:  J Am Chem Soc       Date:  2017-12-28       Impact factor: 15.419

6.  Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates.

Authors:  Derick R White; Evan C Bornowski; John P Wolfe
Journal:  Isr J Chem       Date:  2020-01-24       Impact factor: 3.333

7.  Diethylzinc-Mediated Metalloamination-Alkylation of N, N-Dimethylhydrazinoalkenes. Catalysis of C-Zn Alkylation Using Simple Cu(I) Salts.

Authors:  Ky Mickelsen; Sean Zabawa; Tom Livinghouse
Journal:  Synlett       Date:  2017-10-12       Impact factor: 2.454

8.  Nickel-Catalyzed Dearomative trans-1,2-Carboamination.

Authors:  Lucas W Hernandez; Ulrich Klöckner; Jola Pospech; Lilian Hauss; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

9.  Pd-Catalyzed Alkene Carboheteroarylation Reactions for the Synthesis of 3-Cyclopentylindole Derivatives.

Authors:  Janelle K Kirsch; Jenna L Manske; John P Wolfe
Journal:  J Org Chem       Date:  2018-10-10       Impact factor: 4.354

10.  Rh(iii)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes.

Authors:  Chao Chen; Chen Shi; Yaxi Yang; Bing Zhou
Journal:  Chem Sci       Date:  2020-10-16       Impact factor: 9.825

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