Literature DB >> 19072966

Enantioselective iridium-catalyzed allylic arylation.

Damien Polet1, Xavier Rathgeb, Caroline A Falciola, Jean-Baptiste Langlois, Samir El Hajjaji, Alexandre Alexakis.   

Abstract

We describe herein the development of the first iridium-catalyzed allylic substitution using arylzinc nucleophiles. High enantioselectivities were obtained from the reactions, which used commercially available Grignard reagents as the starting materials. This methodology was also shown to be compatible with halogen/metal exchange reactions. Its synthetic potential is demonstrated by its application towards the formal synthesis of (+)-sertraline.

Entities:  

Year:  2009        PMID: 19072966     DOI: 10.1002/chem.200801879

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  14 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Mechanistically driven development of iridium catalysts for asymmetric allylic substitution.

Authors:  John F Hartwig; Levi M Stanley
Journal:  Acc Chem Res       Date:  2010-09-28       Impact factor: 22.384

3.  Site- and enantioselective formation of allene-bearing tertiary or quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution.

Authors:  Byunghyuck Jung; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-03       Impact factor: 15.419

4.  Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-17       Impact factor: 15.336

5.  Copper-catalyzed enantioselective allylic substitution with readily accessible carbonyl- and acetal-containing vinylboron reagents.

Authors:  Fang Gao; James L Carr; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-25       Impact factor: 15.336

6.  Quaternary carbon stereogenic centers through copper-catalyzed enantioselective allylic substitutions with readily accessible aryl- or heteroaryllithium reagents and aluminum chlorides.

Authors:  Fang Gao; Yunmi Lee; Kyoko Mandai; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-02       Impact factor: 15.336

7.  Iridium-catalyzed kinetic asymmetric transformations of racemic allylic benzoates.

Authors:  Levi M Stanley; Chen Bai; Mitsuhiro Ueda; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

8.  Iridium-catalyzed enantioselective allylic substitution of unstabilized enolates derived from α,β-unsaturated ketones.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-10       Impact factor: 15.336

9.  Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

Authors:  Ming Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-10-23       Impact factor: 15.419

10.  Iridium-catalyzed regioselective and enantioselective allylation of trimethylsiloxyfuran.

Authors:  Wenyong Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2012-09-11       Impact factor: 15.419

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