Literature DB >> 20976023

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

Sherry R Chemler1.   

Abstract

The enantioselective intramolecular aminative functionalization of unactivated alkenes and related π-systems is a straight-forward and atom economical strategy for the n class="Gene">synthesis of chiral nitrogen heterocycles. These reactions can be categorized as oxidatively neutral, such as alkene hydroamination, or as oxidative reactions, such as alkene difunctionalization, e.g. aminooxygenation and carboamination. This perspective reviews the current work in the field and explores mechanistic trends that are common among the different catalysts and reaction types.

Entities:  

Year:  2009        PMID: 20976023      PMCID: PMC2957828          DOI: 10.1039/B907743J

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  38 in total

1.  Exceptional rate enhancements and improved diastereoselectivities through chelating diamide coordination in intramolecular alkene hydroaminations catalyzed by yttrium and neodymium amido complexes.

Authors:  Young Kwan Kim; Tom Livinghouse
Journal:  Angew Chem Int Ed Engl       Date:  2002-10-04       Impact factor: 15.336

2.  Enantioselective catalytic hydroamination of alkenes.

Authors:  Peter W Roesky; Thomas E Müller
Journal:  Angew Chem Int Ed Engl       Date:  2003-06-23       Impact factor: 15.336

3.  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

4.  Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes.

Authors:  Zhibin Zhang; Christopher F Bender; Ross A Widenhoefer
Journal:  J Am Chem Soc       Date:  2007-10-30       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.  Recent developments in enantioselective gold(I) catalysis.

Authors:  Ross A Widenhoefer
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

7.  Copper(II) acetate promoted intramolecular diamination of unactivated olefins.

Authors:  Thomas P Zabawa; Dhanalakshmi Kasi; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

8.  Catalytic asymmetric hydroamination of non-activated olefins.

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

9.  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

10.  Palladium-catalyzed aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions.

Authors:  Vasily Kotov; Christopher C Scarborough; Shannon S Stahl
Journal:  Inorg Chem       Date:  2007-03-19       Impact factor: 5.165

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  32 in total

1.  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

Review 2.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

3.  Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors:  Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal:  Org Lett       Date:  2018-11-08       Impact factor: 6.005

4.  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

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.  Rhodium-catalyzed asymmetric intramolecular hydroamination of unactivated alkenes.

Authors:  Xiaoqiang Shen; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

7.  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

8.  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

9.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

10.  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

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