Literature DB >> 22257169

Copper-catalyzed enantioselective intramolecular alkene amination/intermolecular Heck-type coupling cascade.

Timothy W Liwosz1, Sherry R Chemler.   

Abstract

Enantioselective copper-catalyzed cyclization of γ-alkenylsulfonamides and a δ-alkenylsulfonamide in the presence of a range of vinyl arenes results in variously functionalized 2-substituted chiral nitrogen heterocycles via a formal alkene C-H functionalization process. Application of this reaction to the concise synthesis of a 5-HT(7) receptor antagonist is demonstrated.
© 2012 American Chemical Society

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22257169      PMCID： PMC3314298          DOI： 10.1021/ja211272v

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


  38 in total

1.  A novel, potent, and selective 5-HT(7) antagonist: (R)-3-(2-(2-(4-methylpiperidin-1-yl)ethyl)pyrrolidine-1-sulfonyl) phen ol (SB-269970).

Authors:  P J Lovell; S M Bromidge; S Dabbs; D M Duckworth; I T Forbes; A J Jennings; F D King; D N Middlemiss; S K Rahman; D V Saunders; L L Collin; J J Hagan; G J Riley; D R Thomas
Journal:  J Med Chem       Date:  2000-02-10       Impact factor: 7.446

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.  Copper-promoted and copper-catalyzed intermolecular alkene diamination.

Authors:  Fatima C Sequeira; Benjamin W Turnpenny; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-23       Impact factor: 15.336

4.  Optimization of substituted N-3-benzylimidazoquinazolinone sulfonamides as potent and selective PDE5 inhibitors.

Authors:  D P Rotella; Z Sun; Y Zhu; J Krupinski; R Pongrac; L Seliger; D Normandin; J E Macor
Journal:  J Med Chem       Date:  2000-12-28       Impact factor: 7.446

5.  Potent and selective nonpeptide inhibitors of caspases 3 and 7.

Authors:  D Lee; S A Long; J H Murray; J L Adams; M E Nuttall; D P Nadeau; K Kikly; J D Winkler; C M Sung; M D Ryan; M A Levy; P M Keller; W E DeWolf
Journal:  J Med Chem       Date:  2001-06-07       Impact factor: 7.446

6.  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

7.  Distinct reactivity of Pd(OTs)2: the intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes.

Authors:  Chris E Houlden; Chris D Bailey; J Gair Ford; Michel R Gagné; Guy C Lloyd-Jones; Kevin I Booker-Milburn
Journal:  J Am Chem Soc       Date:  2008-07-10       Impact factor: 15.419

8.  Direct cross-coupling reaction of simple alkenes with acrylates catalyzed by palladium catalyst.

Authors:  Yun-He Xu; Jun Lu; Teck-Peng Loh
Journal:  J Am Chem Soc       Date:  2009-02-04       Impact factor: 15.419

9.  Cobalt dinitrosoalkane complexes in the C-H functionalization of olefins.

Authors:  Jennifer M Schomaker; W Christopher Boyd; Ian C Stewart; F Dean Toste; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2008-03-05       Impact factor: 15.419

10.  Palladium-catalyzed carboamination of alkenes promoted by N-fluorobenzenesulfonimide via C-H activation of arenes.

Authors:  Carolyn F Rosewall; Paul A Sibbald; Dmitry V Liskin; Forrest E Michael
Journal:  J Am Chem Soc       Date:  2009-07-15       Impact factor: 15.419
View more
  38 in total

1.  Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

Authors:  Yan Miller; Lei Miao; Azade S Hosseini; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2012-07-05       Impact factor: 15.419

2.  Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides.

Authors:  Paul T Marcyk; Latisha R Jefferies; Deyaa I AbuSalim; Maren Pink; Mu-Hyun Baik; Silas P Cook
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-15       Impact factor: 15.336

3.  Highly enantioselective dearomatizing formal [3+3] cycloaddition reactions of N-acyliminopyridinium ylides with electrophilic enol carbene intermediates.

Authors:  Xinfang Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

4.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

5.  3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.

Authors:  Emilia J Groso; Alexander N Golonka; Ryan A Harding; Brandon W Alexander; Taylor M Sodano; Corinna S Schindler
Journal:  ACS Catal       Date:  2018-01-18       Impact factor: 13.084

6.  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

7.  6-Azabicyclo[3.2.1]octanes Via Copper-Catalyzed Enantioselective Alkene Carboamination.

Authors:  Barbara J Casavant; Azade S Hosseini; Sherry R Chemler
Journal:  Adv Synth Catal       Date:  2014-08-11       Impact factor: 5.837

8.  Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines.

Authors:  Benjamin W Turnpenny; Sherry R Chemler
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

9.  Chiral Indoline Synthesis Via Enantioselective Intramolecular Copper-Catalyzed Alkene Hydroamination.

Authors:  Benjamin W Turnpenny; Kiante L Hyman; Sherry R Chemler
Journal:  Organometallics       Date:  2012-08-27       Impact factor: 3.876

10.  Mechanistic analysis and optimization of the copper-catalyzed enantioselective intramolecular alkene aminooxygenation.

Authors:  Monissa C Paderes; Jerome B Keister; Sherry R Chemler
Journal:  J Org Chem       Date:  2012-12-28       Impact factor: 4.354
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.