Literature DB >> 22594398

Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings.

Michael J Ardolino1, James P Morken.   

Abstract

The palladium-catalyzed cross-coupling of chiral propargyl acetates and allyl boronates delivers chiral 1,5-enynes with excellent levels of chirality transfer and can be applied across a broad range of substrates.

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Year:  2012        PMID： 22594398      PMCID： PMC3374959          DOI： 10.1021/ja302329f

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


  25 in total

1.  Gold(III)-catalyzed nucleophilic substitution of propargylic alcohols.

Authors:  Marie Georgy; Valérie Boucard; Jean-Marc Campagne
Journal:  J Am Chem Soc       Date:  2005-10-19       Impact factor: 15.419

2.  Ni- and Pd-catalyzed synthesis of substituted and functionalized allylic boronates.

Authors:  Ping Zhang; Ian A Roundtree; James P Morken
Journal:  Org Lett       Date:  2012-02-29       Impact factor: 6.005

3.  Generation of cations from alkoxides: allylation of propargyl alcohols.

Authors:  George W Kabalka; Min-Liang Yao; Scott Borella
Journal:  J Am Chem Soc       Date:  2006-09-06       Impact factor: 15.419

Review 4.  The discovery of novel reactivity in the development of C-C bond-forming reactions: in situ generation of zinc acetylides with Zn(II)/R(3)N.

Authors:  D E Frantz; R Fassler; C S Tomooka; E M Carreira
Journal:  Acc Chem Res       Date:  2000-06       Impact factor: 22.384

5.  Novel carbon-carbon bond-forming reactions using carbocations produced from substituted propargyl silyl ethers by the action of TMSOTf.

Authors:  T Ishikawa; M Okano; T Aikawa; S Saito
Journal:  J Org Chem       Date:  2001-06-29       Impact factor: 4.354

6.  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

7.  Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenes.

Authors:  Michael R Luzung; Jordan P Markham; F Dean Toste
Journal:  J Am Chem Soc       Date:  2004-09-08       Impact factor: 15.419

8.  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

9.  Iron-catalyzed 1,4-hydroboration of 1,3-dienes.

Authors:  Jessica Y Wu; Benoît Moreau; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

10.  Palladium(0)-catalyzed synthesis of chiral ene-allenes using alkenyl trifluoroborates.

Authors:  Gary A Molander; Erin M Sommers; Sharon R Baker
Journal:  J Org Chem       Date:  2006-02-17       Impact factor: 4.354
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  10 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.  Enantioselective and Diastereodivergent Allylation of Propargylic C-H Bonds.

Authors:  Jin Zhu; Yidong Wang; Aaron D Charlack; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2022-08-17       Impact factor: 16.383

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

Authors:  Hai Le; Robert E Kyne; Laura A Brozek; James P Morken
Journal:  Org Lett       Date:  2013-03-19       Impact factor: 6.005

6.  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

7.  Palladium-catalysed formation of vicinal all-carbon quaternary centres via propargylation.

Authors:  Xin Huang; Shangze Wu; Wangteng Wu; Pengbin Li; Chunling Fu; Shengming Ma
Journal:  Nat Commun       Date:  2016-08-25       Impact factor: 14.919

8.  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

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.  Palladium/N-heterocyclic carbene catalysed regio and diastereoselective reaction of ketones with allyl reagents via inner-sphere mechanism.

Authors:  Da-Chang Bai; Fei-Le Yu; Wan-Ying Wang; Di Chen; Hao Li; Qing-Rong Liu; Chang-Hua Ding; Bo Chen; Xue-Long Hou
Journal:  Nat Commun       Date:  2016-06-10       Impact factor: 14.919
  10 in total

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