Literature DB >> 27310927

Modular, Catalytic Enantioselective Construction of Quaternary Carbon Stereocenters by Sequential Cross-Coupling Reactions.

Bowman Potter1, Emma K Edelstein1, James P Morken1.   

Abstract

The catalytic Suzuki-Miyaura cross-coupling with chiral γ,γ-disubstituted allylboronates in the presence of RuPhos ligand occurs with high regioselectivity and enantiospecificity, furnishing nonracemic compounds with quaternary centers. Mechanistic experiments suggest that the reaction occurs by transmetalation with allyl migration, followed by rapid reductive elimination.

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Year:  2016        PMID： 27310927      PMCID： PMC5510877          DOI： 10.1021/acs.orglett.6b01580

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  23 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.  Efficient pd-catalyzed amination of heteroaryl halides.

Authors:  Mark D Charles; Phillip Schultz; Stephen L Buchwald
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

3.  Metal-catalyzed ring-opening of alkylidenecyclopropanes: new access to building blocks with an acyclic quaternary stereogenic center.

Authors:  Samah Simaan; Alexander F G Goldberg; Stephane Rosset; Ilan Marek
Journal:  Chemistry       Date:  2010-01-18       Impact factor: 5.236

4.  Enantiospecific sp(2)-sp(3) coupling of secondary and tertiary boronic esters.

Authors:  Amadeu Bonet; Marcin Odachowski; Daniele Leonori; Stephanie Essafi; Varinder K Aggarwal
Journal:  Nat Chem       Date:  2014-06-08       Impact factor: 24.427

5.  Catalytic enantioselective synthesis of quaternary carbon stereocentres.

Authors:  Kyle W Quasdorf; Larry E Overman
Journal:  Nature       Date:  2014-12-11       Impact factor: 49.962

6.  Stereodivergent quaternization of 2-alkyl-2-p-tolylsulfinylacetonitriles: NMR spectroscopic evidence of planar and pyramidal benzylic carbanions.

Authors:  José Luis García Ruano; Ana M Martín-Castro; Francisco Tato; Esther Torrente; Ana M Poveda
Journal:  Chemistry       Date:  2010-06-01       Impact factor: 5.236

7.  All-carbon quaternary stereogenic centers in acyclic systems through the creation of several C-C bonds per chemical step.

Authors:  Ilan Marek; Yury Minko; Morgane Pasco; Tom Mejuch; Noga Gilboa; Helena Chechik; Jaya P Das
Journal:  J Am Chem Soc       Date:  2014-02-10       Impact factor: 15.419

8.  Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution.

Authors:  Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2014-04-29       Impact factor: 15.419

9.  A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates.

Authors:  Chunrui Sun; Bowman Potter; James P Morken
Journal:  J Am Chem Soc       Date:  2014-02-24       Impact factor: 15.419

10.  Enantioselective carbocycle formation through intramolecular Pd-catalyzed allyl-aryl cross-coupling.

Authors:  Christopher H Schuster; John R Coombs; Zachary A Kasun; James P Morken
Journal:  Org Lett       Date:  2014-08-08       Impact factor: 6.005
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  14 in total

1.  Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Authors:  Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

2.  Enantioselective Synthesis of Nonracemic Geminal Silylboronates by Pt-Catalyzed Hydrosilylation.

Authors:  Adam A Szymaniak; Chenlong Zhang; John R Coombs; James P Morken
Journal:  ACS Catal       Date:  2018-02-23       Impact factor: 13.084

3.  Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.

Authors:  Joseph M Zanghi; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

4.  Stereospecific, Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Allylic Pivalates To Deliver Quaternary Stereocenters.

Authors:  Kelsey M Cobb; Javon M Rabb-Lynch; Megan E Hoerrner; Alex Manders; Qi Zhou; Mary P Watson
Journal:  Org Lett       Date:  2017-08-07       Impact factor: 6.005

5.  Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents.

Authors:  Emma K Edelstein; Sheila Namirembe; James P Morken
Journal:  J Am Chem Soc       Date:  2017-03-29       Impact factor: 15.419

6.  Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles.

Authors:  Xinghua Ma; Benjamin Murray; Mark R Biscoe
Journal:  Nat Rev Chem       Date:  2020-09-24       Impact factor: 34.035

7.  Practical, Broadly Applicable, α-Selective, Z-Selective, Diastereoselective, and Enantioselective Addition of Allylboron Compounds to Mono-, Di-, Tri-, and Polyfluoroalkyl Ketones.

Authors:  Farid W van der Mei; Changming Qin; Ryan J Morrison; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2017-06-24       Impact factor: 15.419

8.  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

9.  Diastereo-, Enantio-, and anti-Selective Formation of Secondary Alcohol and Quaternary Carbon Stereocenters by Cu-Catalyzed Additions of B-Substituted Allyl Nucleophiles to Carbonyls.

Authors:  Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal:  Org Lett       Date:  2020-11-18       Impact factor: 6.005

10.  Nickel-Catalyzed, Stereospecific C-C and C-B Cross-Couplings via C-N and C-O Bond Activation.

Authors:  Jianyu Xu; Olivia P Bercher; Michael R Talley; Mary P Watson
Journal:  ACS Catal       Date:  2021-01-19       Impact factor: 13.084
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