Literature DB >> 15315429

A palladium-catalyzed enantioselective alkylative desymmetrization of meso-succinic anhydrides.

Eric A Bercot1, Tomislav Rovis.   

Abstract

Monoalkylation of cyclic anhydrides provides an opportunity to couple a carbon-carbon bond-forming event with the control of backbone stereochemistry. We have developed a palladium-JOSIPHOS catalyst system that desymmetrizes meso-succinic anhydrides using organozinc reagents as nucleophiles, and have found that, in many cases, this reaction proceeds at ambient temperature.

Entities:  

Year:  2004        PMID: 15315429     DOI: 10.1021/ja046528b

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


  7 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.  Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates.

Authors:  Meredith S Eno; Alexander Lu; James P Morken
Journal:  J Am Chem Soc       Date:  2016-06-16       Impact factor: 15.419

3.  Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors:  Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2020-09-10       Impact factor: 13.084

4.  Breaking Amides using Nickel Catalysis.

Authors:  Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

5.  Nickel-Catalyzed Alkylation of Amide Derivatives.

Authors:  Bryan J Simmons; Nicholas A Weires; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2016-04-12       Impact factor: 13.084

6.  Dual Nickel- and Photoredox-Catalyzed Enantioselective Desymmetrization of Cyclic meso-Anhydrides.

Authors:  Erin E Stache; Tomislav Rovis; Abigail G Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-23       Impact factor: 15.336

7.  Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of Aliphatic Amides on the Benchtop.

Authors:  Milauni M Mehta; Timothy B Boit; Jacob E Dander; Neil K Garg
Journal:  Org Lett       Date:  2019-10-17       Impact factor: 6.005

  7 in total

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