Literature DB >> 28489371

Nickel-Catalyzed Cross-Coupling of Vinyl Dioxanones to Form Enantiomerically Enriched Cyclopropanes.

Yi-An Guo1, Tao Liang1, Seung Wook Kim1, Hongde Xiao1, Michael J Krische1.   

Abstract

Under the conditions of nickel(0) catalysis, enantiomerically enriched vinyl dioxanones engage boroxines or B2(pin)2 in stereospecific cross-coupling to form diverse tetrasubstituted cyclopropanes bearing all-carbon quaternary stereocenters. The collective data corroborate a mechanism involving nickel(0)-mediated benzylic oxidative addition with inversion of stereochemistry followed by reversible olefin insertion to form a (cyclopropylcarbinyl)nickel complex, which upon reductive elimination releases the cyclopropane.

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Year:  2017        PMID： 28489371      PMCID： PMC5651680          DOI： 10.1021/jacs.7b03371

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


  31 in total

Review 1.  Biosynthesis and metabolism of cyclopropane rings in natural compounds.

Authors:  Ludger A Wessjohann; Wolfgang Brandt; Thies Thiemann
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

Review 2.  New and unusual scaffolds in medicinal chemistry.

Authors:  Charles M Marson
Journal:  Chem Soc Rev       Date:  2011-08-12       Impact factor: 54.564

3.  Paraformaldehyde and methanol as C1  feedstocks in metal-catalyzed C-C couplings of π-unsaturated reactants: beyond hydroformylation.

Authors:  Brannon Sam; Bernhard Breit; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-27       Impact factor: 15.336

4.  Enantioselective Synthesis of Oxetanes Bearing All-Carbon Quaternary Stereocenters via Iridium-Catalyzed C-C Bond-Forming Transfer Hydrogenation.

Authors:  Yi-An Guo; Wonchul Lee; Michael J Krische
Journal:  Chemistry       Date:  2017-01-27       Impact factor: 5.236

5.  The "Cyclopropyl Fragment" is a Versatile Player that Frequently Appears in Preclinical/Clinical Drug Molecules.

Authors:  Tanaji T Talele
Journal:  J Med Chem       Date:  2016-06-30       Impact factor: 7.446

Review 6.  Recent advances in homogeneous nickel catalysis.

Authors:  Sarah Z Tasker; Eric A Standley; Timothy F Jamison
Journal:  Nature       Date:  2014-05-15       Impact factor: 49.962

7.  Enantiospecific intramolecular Heck reactions of secondary benzylic ethers.

Authors:  Michael R Harris; Mikhail O Konev; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2014-05-23       Impact factor: 15.419

8.  Redox-triggered C-C coupling of alcohols and vinyl epoxides: diastereo- and enantioselective formation of all-carbon quaternary centers via tert-(hydroxy)-prenylation.

Authors:  Jiajie Feng; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2014-06-10       Impact factor: 15.419

9.  Single-Electron Transmetalation via Photoredox/Nickel Dual Catalysis: Unlocking a New Paradigm for sp(3)-sp(2) Cross-Coupling.

Authors:  John C Tellis; Christopher B Kelly; David N Primer; Matthieu Jouffroy; Niki R Patel; Gary A Molander
Journal:  Acc Chem Res       Date:  2016-07-05       Impact factor: 22.384

10.  Stereospecific Cross Couplings To Set Benzylic, All-Carbon Quaternary Stereocenters in High Enantiopurity.

Authors:  Qi Zhou; Kelsey M Cobb; Tianyu Tan; Mary P Watson
Journal:  J Am Chem Soc       Date:  2016-09-09       Impact factor: 15.419
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  5 in total

1.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

2.  Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.

Authors:  Shuo-Qing Zhang; Buck L H Taylor; Chong-Lei Ji; Yuan Gao; Michael R Harris; Luke E Hanna; Elizabeth R Jarvo; K N Houk; Xin Hong
Journal:  J Am Chem Soc       Date:  2017-09-07       Impact factor: 15.419

Review 3.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

4.  Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

Authors:  Sarah M Pound; Mary P Watson
Journal:  Chem Commun (Camb)       Date:  2018-10-30       Impact factor: 6.222

5.  Enantioselective Total Synthesis of Andrographolide and 14-Hydroxy-Colladonin: Carbonyl Reductive Coupling and trans-Decalin Formation by Hydrogen Transfer.

Authors:  Lin Yang; Thomas Wurm; Binit Sharma Poudel; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2020-10-15       Impact factor: 15.336
  5 in total

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