Literature DB >> 19678678

Highly enantioselective synthesis of chiral secondary amines by gold(I)/chiral Brønsted acid catalyzed tandem intermolecular hydroamination and transfer hydrogenation reactions.

Xin-Yuan Liu1, Chi-Ming Che.   

Abstract

A method for the synthesis of enantiomerically enriched secondary amines with excellent ee values through the tandem intermolecular hydroamination/transfer hydrogenation of alkynes using a "gold(I) complex-chiral Brønsted acid" protocol is developed. The catalysis works for a wide variety of aryl, alkenyl, and aliphatic alkynes as well as anilines with different electronic properties.

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Year:  2009        PMID： 19678678     DOI： 10.1021/ol901443b

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


  10 in total

1.  An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

Authors:  David M Rubush; Michelle A Morges; Barbara J Rose; Douglas H Thamm; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419

2.  Intramolecular hydroamination of alkynic sulfonamides catalyzed by a gold-triethynylphosphine complex: Construction of azepine frameworks by 7-exo-dig cyclization.

Authors:  Hideto Ito; Tomoya Harada; Hirohisa Ohmiya; Masaya Sawamura
Journal:  Beilstein J Org Chem       Date:  2011-07-08       Impact factor: 2.883

3.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

4.  Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses.

Authors:  Yin-Wei Sun; Qin Xu; Min Shi
Journal:  Beilstein J Org Chem       Date:  2013-10-28       Impact factor: 2.883

5.  Integration of aerobic oxidation and intramolecular asymmetric aza-Friedel-Crafts reactions with a chiral bifunctional heterogeneous catalyst.

Authors:  Hong-Gang Cheng; Javier Miguélez; Hiroyuki Miyamura; Woo-Jin Yoo; Shū Kobayashi
Journal:  Chem Sci       Date:  2016-10-05       Impact factor: 9.825

6.  Bifunctional catalysis: direct reductive amination of aliphatic ketones with an iridium-phosphate catalyst.

Authors:  Barbara Villa-Marcos; Chaoqun Li; Keith R Mulholland; Philip J Hogan; Jianliang Xiao
Journal:  Molecules       Date:  2010-04-08       Impact factor: 4.411

7.  H-Bonded Counterion-Directed Enantioselective Au(I) Catalysis.

Authors:  Allegra Franchino; Àlex Martí; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2022-02-09       Impact factor: 15.419

8.  Anatomy of gold catalysts: facts and myths.

Authors:  Beatrice Ranieri; Imma Escofet; Antonio M Echavarren
Journal:  Org Biomol Chem       Date:  2015-06-09       Impact factor: 3.876

9.  Gold and BINOL-phosphoric acid catalyzed enantioselective hydroamination/N-sulfonyliminium cyclization cascade.

Authors:  Alex W Gregory; Pavol Jakubec; Paul Turner; Darren J Dixon
Journal:  Org Lett       Date:  2013-08-28       Impact factor: 6.005

10.  Highly Stereoselective Synthesis of Polycyclic Indoles through Rearrangement/[4+2] Cycloaddition under Sequential Catalysis.

Authors:  Di-Han Zhang; Min Shi
Journal:  ChemistryOpen       Date:  2012-09-11       Impact factor: 2.911
  10 in total

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