Literature DB >> 23350620

Copper-catalyzed enantioselective allyl-allyl cross-coupling.

Valentín Hornillos1, Manuel Pérez, Martín Fañanás-Mastral, Ben L Feringa.   

Abstract

A Cu(I)-phosphoramidite-based catalytic system that allows asymmetric allyl-allyl cross-coupling with high enantioselectivity is reported. This transformation tolerates a large variety of functionalized substrates. The versatility of this new reaction is illustrated in the catalytic asymmetric synthesis of the Martinelline alkaloids chromene derivative core.

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Year:  2013        PMID: 23350620     DOI: 10.1021/ja312487r

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


  11 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.  Evaluation of Chromane-Based Bryostatin Analogues Prepared via Hydrogen-Mediated C-C Bond Formation: Potency Does Not Confer Bryostatin-like Biology.

Authors:  John M Ketcham; Ivan Volchkov; Te-Yu Chen; Peter M Blumberg; Noemi Kedei; Nancy E Lewin; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-09-27       Impact factor: 15.419

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.  Multifunctional organoboron compounds for scalable natural product synthesis.

Authors:  Fanke Meng; Kevin P McGrath; Amir H Hoveyda
Journal:  Nature       Date:  2014-09-18       Impact factor: 49.962

6.  Catalytic enantioselective 1,6-conjugate additions of propargyl and allyl groups.

Authors:  Fanke Meng; Xiben Li; Sebastian Torker; Ying Shi; Xiao Shen; Amir H Hoveyda
Journal:  Nature       Date:  2016-08-01       Impact factor: 49.962

Review 7.  Enantioselective copper catalysed, direct functionalisation of allenes via allyl copper intermediates.

Authors:  Alexander P Pulis; Kay Yeung; David J Procter
Journal:  Chem Sci       Date:  2017-06-08       Impact factor: 9.825

8.  A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes.

Authors:  Ding-Wei Ji; Yan-Cheng Hu; Hao Zheng; Chao-Yang Zhao; Qing-An Chen; Vy M Dong
Journal:  Chem Sci       Date:  2019-05-16       Impact factor: 9.825

9.  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

Review 10.  Recent advances in copper-catalyzed asymmetric coupling reactions.

Authors:  Fengtao Zhou; Qian Cai
Journal:  Beilstein J Org Chem       Date:  2015-12-15       Impact factor: 2.883

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