Literature DB >> 34354327

Harnessing C-O Bonds in Stereoselective Cross-Coupling and Cross-Electrophile Coupling Reactions.

Amberly B Sanford1, Elizabeth R Jarvo1.   

Abstract

Herein, we discuss our laboratory's research in the activation of alcohol derivatives in cross-coupling and cross-electrophile coupling reactions. Our developed methods enable the use of secondary alcohols to afford tertiary stereogenic centers, which we applied to the synthesis of pharmaceutically relevant compounds and substructures. We first discuss the synthesis of bioactive compounds via stereospecific Kumada cross-coupling reactions, followed by a discussion on the development of our stereoselective cross-electrophile coupling reaction to synthesize cyclopropanes.

Entities:  

Keywords:  asymmetric synthesis; cross-coupling; cross-electrophile coupling; enantioselective synthesis; nickel

Year:  2020        PMID: 34354327      PMCID: PMC8329764          DOI: 10.1055/s-0040-1705987

Source DB:  PubMed          Journal:  Synlett        ISSN: 0936-5214            Impact factor:   2.454


  41 in total

1.  The first direct and enantioselective cross-aldol reaction of aldehydes.

Authors:  Alan B Northrup; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2002-06-19       Impact factor: 15.419

Review 2.  Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

Authors:  Brad M Rosen; Kyle W Quasdorf; Daniella A Wilson; Na Zhang; Ana-Maria Resmerita; Neil K Garg; Virgil Percec
Journal:  Chem Rev       Date:  2010-12-06       Impact factor: 60.622

Review 3.  Molecular Complexity as a Driver for Chemical Process Innovation in the Pharmaceutical Industry.

Authors:  Seb Caille; Sheng Cui; Margaret M Faul; Steven M Mennen; Jason S Tedrow; Shawn D Walker
Journal:  J Org Chem       Date:  2019-04-10       Impact factor: 4.354

Review 4.  Cyclopropanation Strategies in Recent Total Syntheses.

Authors:  Christian Ebner; Erick M Carreira
Journal:  Chem Rev       Date:  2017-05-03       Impact factor: 60.622

5.  Stereospecific Cross-Coupling Reactions Provide Conformationally-Biased Arylalkanes with Anti-Leukemia Activity.

Authors:  Amberly B Sanford; Emily J Tollefson; Elizabeth R Jarvo
Journal:  Isr J Chem       Date:  2019-09-06       Impact factor: 3.333

6.  Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst.

Authors:  Michael R Harris; Luke E Hanna; Margaret A Greene; Curtis E Moore; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2013-02-22       Impact factor: 15.419

Review 7.  Chemoselective hydroxyl group transformation: an elusive target.

Authors:  Darci J Trader; Erin E Carlson
Journal:  Mol Biosyst       Date:  2012-10

8.  Identification of the Active Catalyst for Nickel-Catalyzed Stereospecific Kumada Coupling Reactions of Ethers.

Authors:  David D Dawson; Victoria F Oswald; Andy S Borovik; Elizabeth R Jarvo
Journal:  Chemistry       Date:  2020-02-21       Impact factor: 5.236

9.  Stereospecific cross-coupling reactions of aryl-substituted tetrahydrofurans, tetrahydropyrans, and lactones.

Authors:  Emily J Tollefson; David D Dawson; Charlotte A Osborne; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2014-10-13       Impact factor: 15.419

10.  Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Benzylic Ethers with Isotopically-Labeled Grignard Reagents.

Authors:  David D Dawson; Elizabeth R Jarvo
Journal:  Org Process Res Dev       Date:  2015-09-11       Impact factor: 3.317

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