Literature DB >> 23510460

Catalytic enantioselective allyl-allyl cross-coupling with a borylated allylboronate.

Hai Le1, Robert E Kyne, Laura A Brozek, James P Morken.   

Abstract

Catalytic enantioselective allyl-allyl cross-coupling of a borylated allylboronate reagent gives versatile borylated chiral 1,5-hexadienes. These compounds may be manipulated in a number of useful ways to give functionalized chiral building blocks for asymmetric synthesis.

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Year:  2013        PMID： 23510460      PMCID： PMC3663875          DOI： 10.1021/ol400088g

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


  32 in total

1.  Unusual diboration of allenes catalyzed by palladium complexes and organic iodides: a new efficient route to biboronic compounds.

Authors:  F Y Yang; C H Cheng
Journal:  J Am Chem Soc       Date:  2001-01-31       Impact factor: 15.419

2.  A rationally designed universal catalyst for Suzuki-Miyaura coupling processes.

Authors:  Shawn D Walker; Timothy E Barder; Joseph R Martinelli; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2004-03-26       Impact factor: 15.336

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.  Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors:  Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

5.  Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides.

Authors:  Laura A Brozek; Michael J Ardolino; James P Morken
Journal:  J Am Chem Soc       Date:  2011-10-05       Impact factor: 15.419

6.  Palladium(0) versus nickel(0) catalysis in selective functional-group-tolerant sp(3)-sp(3) carbon-carbon bond formations.

Authors:  Emmanuel Ferrer Flegeau; Uwe Schneider; Shū Kobayashi
Journal:  Chemistry       Date:  2009-11-16       Impact factor: 5.236

7.  Nickel-catalyzed allylation of allyl carbonates with homoallyl alcohols via retro-allylation providing 1,5-hexadienes.

Authors:  Yuto Sumida; Sayuri Hayashi; Koji Hirano; Hideki Yorimitsu; Koichiro Oshima
Journal:  Org Lett       Date:  2008-03-21       Impact factor: 6.005

8.  Synthesis of (E,Z)-1-alkoxy-3-acyloxy-2-methylpenta-1,3-dienes via Danishefsky-type dienes or O-acylation of enones.

Authors:  Sylvain Laclef; Claudia J Exner; Maris Turks; Valeria Videtta; Pierre Vogel
Journal:  J Org Chem       Date:  2009-11-20       Impact factor: 4.354

9.  Copper-promoted coupling of vinyl boronates and alcohols: a mild synthesis of allyl vinyl ethers.

Authors:  Ryan E Shade; Alan M Hyde; John-Carl Olsen; Craig A Merlic
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

10.  Unusual allylpalladium carboxylate complexes: identification of the resting state of catalytic enantioselective decarboxylative allylic alkylation reactions of ketones.

Authors:  Nathaniel H Sherden; Douglas C Behenna; Scott C Virgil; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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  12 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.  Branched/linear selectivity in palladium-catalyzed allyl-allyl cross-couplings: The role of ligands.

Authors:  Michael J Ardolino; James P Morken
Journal:  Tetrahedron       Date:  2015-09-16       Impact factor: 2.457

3.  Protecting group-free, selective cross-coupling of alkyltrifluoroborates with borylated aryl bromides via photoredox/nickel dual catalysis.

Authors:  Yohei Yamashita; John C Tellis; Gary A Molander
Journal:  Proc Natl Acad Sci U S A       Date:  2015-09-14       Impact factor: 11.205

4.  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

5.  Stereocontrol in Palladium-Catalyzed Propargylic Substitutions: Kinetic Resolution to give Enantioenriched 1,5-Enynes and Propargyl Acetates.

Authors:  Michael J Ardolino; Meredith S Eno; James P Morken
Journal:  Adv Synth Catal       Date:  2013-11-25       Impact factor: 5.837

6.  Catalytic enantioselective protoboration of disubstituted allenes. Access to alkenylboron compounds in high enantiomeric purity.

Authors:  Hwanjong Jang; Byunghyuck Jung; Amir H Hoveyda
Journal:  Org Lett       Date:  2014-08-25       Impact factor: 6.005

7.  Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with AllylB(pin).

Authors:  Hai Le; Amanda Batten; James P Morken
Journal:  Org Lett       Date:  2014-04-04       Impact factor: 6.005

8.  Mechanistic Insights into Carbonyl-Directed Rhodium-Catalyzed Hydroboration: ab Initio Study of a Cyclic γ,δ-Unsaturated Amide.

Authors:  Zhao-Di Yang; Rhitankar Pal; Gia L Hoang; Xiao Cheng Zeng; James M Takacs
Journal:  ACS Catal       Date:  2014-01-22       Impact factor: 13.084

9.  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

10.  Catalytic Borylative Opening of Propargyl Cyclopropane, Epoxide, Aziridine, and Oxetane Substrates: Ligand Controlled Synthesis of Allenyl Boronates and Alkenyl Diboronates.

Authors:  Jian Zhao; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-11       Impact factor: 15.336
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