Literature DB >> 23243332

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

Benjamin W Turnpenny1, Kiante L Hyman, Sherry R Chemler.   

Abstract

An enantioselective copper-catalyzed hydroamination / cyclization of N-sulfonyl-2-allylanilines for the synthesis of chiral 2-methylindolines is reported. Chiral 2-methylindolines are important subunits in drugs and bioactive compounds. This method provides chiral N-sulfonyl-2-methyl indolines in up to 90% ee.

Entities:  

Year:  2012        PMID： 23243332      PMCID： PMC3519432          DOI： 10.1021/om300744m

Source DB:  PubMed          Journal:  Organometallics        ISSN： 0276-7333            Impact factor:   3.876


  25 in total

1.  Kinetic resolutions of indolines by a nonenzymatic acylation catalyst.

Authors:  Forrest O Arp; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2006-11-08       Impact factor: 15.419

2.  The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles.

Authors:  Sherry R Chemler
Journal:  Org Biomol Chem       Date:  2009       Impact factor: 3.876

Review 3.  Asymmetric hydroamination of non-activated carbon-carbon multiple bonds.

Authors:  Isabelle Aillaud; Jacqueline Collin; Jérôme Hannedouche; Emmanuelle Schulz
Journal:  Dalton Trans       Date:  2007-09-07       Impact factor: 4.390

4.  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

Review 5.  Hydroamination: direct addition of amines to alkenes and alkynes.

Authors:  Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal:  Chem Rev       Date:  2008-08-26       Impact factor: 60.622

6.  Catalytic asymmetric hydroamination of non-activated olefins.

Authors:  Kai C Hultzsch
Journal:  Org Biomol Chem       Date:  2005-04-07       Impact factor: 3.876

7.  Copper-catalyzed intermolecular hydroamination of alkenes.

Authors:  Jason G Taylor; Neil Whittall; King Kuok Mimi Hii
Journal:  Org Lett       Date:  2006-08-03       Impact factor: 6.005

8.  Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes.

Authors:  Peter H Fuller; Jin-Woo Kim; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

9.  Cu(I)-catalyzed intramolecular hydroamination of unactivated alkenes bearing a primary or secondary amino group in alcoholic solvents.

Authors:  Hirohisa Ohmiya; Toshimitsu Moriya; Masaya Sawamura
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

10.  Carbonic anhydrase inhibitors. Comparison of chlorthalidone and indapamide X-ray crystal structures in adducts with isozyme II: when three water molecules and the keto-enol tautomerism make the difference.

Authors:  Claudia Temperini; Alessandro Cecchi; Andrea Scozzafava; Claudiu T Supuran
Journal:  J Med Chem       Date:  2009-01-22       Impact factor: 7.446
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  9 in total

1.  Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.

Authors:  Sherry R Chemler; Shuklendu D Karyakarte; Zainab M Khoder
Journal:  J Org Chem       Date:  2017-09-29       Impact factor: 4.354

2.  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

3.  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

4.  Enantioselective thiourea-catalyzed intramolecular cope-type hydroamination.

Authors:  Adam R Brown; Christopher Uyeda; Carolyn A Brotherton; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-04-24       Impact factor: 15.419

5.  Copper-catalyzed oxidative amination and allylic amination of alkenes.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Chemistry       Date:  2013-07-22       Impact factor: 5.236

6.  Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer.

Authors:  Casey B Roos; Joachim Demaerel; David E Graff; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2020-03-20       Impact factor: 15.419

7.  A computational study of the copper(II)-catalyzed enantioselective intramolecular aminooxygenation of alkenes.

Authors:  Lee Belding; Sherry R Chemler; Travis Dudding
Journal:  J Org Chem       Date:  2013-10-01       Impact factor: 4.354

8.  Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses.

Authors:  Yin-Wei Sun; Qin Xu; Min Shi
Journal:  Beilstein J Org Chem       Date:  2013-10-28       Impact factor: 2.883

Review 9.  First-Row Late Transition Metals for Catalytic Alkene Hydrofunctionalisation: Recent Advances in C-N, C-O and C-P Bond Formation.

Authors:  Sophie Bezzenine-Lafollée; Richard Gil; Damien Prim; Jérôme Hannedouche
Journal:  Molecules       Date:  2017-11-04       Impact factor: 4.411
  9 in total

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