Literature DB >> 15069496

Mild and efficient palladium(II)-catalyzed racemization of allenes.

Attila Horvath1, Jan-E Backvall.   

Abstract

Allenes undergo racemization in the presence of catalytic amounts of Pd(OAc)2/LiBr under mild conditions; the reaction proceeds via a bromopalladation-debromopalladation sequence and tolerates various functional groups.

Entities:  

Year:  2004        PMID： 15069496     DOI： 10.1039/b316482a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  8 in total

1.  Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.

Authors:  Nathan J Adamson; Haleh Jeddi; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2019-05-15       Impact factor: 15.419

2.  Scope and mechanistic investigations of Pd-catalyzed coupling/cyclizations and cycloisomerizations of allenyl malonates.

Authors:  Logan E Vine; Ryan D Reeves; Eleanor M Landwehr; Israel Fernández; Jennifer M Schomaker
Journal:  ACS Catal       Date:  2021-07-15       Impact factor: 13.700

3.  Enantioselective synthesis of 5,7-bicyclic ring systems from axially chiral allenes using a Rh(I)-catalyzed cyclocarbonylation reaction.

Authors:  Francois Grillet; Kay M Brummond
Journal:  J Org Chem       Date:  2013-03-29       Impact factor: 4.354

4.  Pd-catalyzed asymmetric β-hydride elimination en route to chiral allenes.

Authors:  Ian T Crouch; Robynne K Neff; Doug E Frantz
Journal:  J Am Chem Soc       Date:  2013-03-19       Impact factor: 15.419

5.  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

6.  Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

Authors:  Youming Huang; Juan Del Pozo; Sebastian Torker; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2018-02-08       Impact factor: 15.419

7.  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

8.  Chiroptical properties and the racemization of pyrene and tetrathiafulvalene-substituted allene: substitution and solvent effects on racemization in tetrathiafulvalenylallene.

Authors:  Masashi Hasegawa; Seiya Iwata; Yasuto Sone; Junta Endo; Hideyo Matsuzawa; Yasuhiro Mazaki
Journal:  Molecules       Date:  2014-03-04       Impact factor: 4.411
  8 in total

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