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Literature DB >> 22892048

Axially chiral triazoloisoquinolin-3-ylidene ligands in gold(I)-catalyzed asymmetric intermolecular (4 + 2) cycloadditions of allenamides and dienes.

Javier Francos¹, Francisca Grande-Carmona, Hélio Faustino, Javier Iglesias-Sigüenza, Elena Díez, Isaac Alonso, Rosario Fernández, José M Lassaletta, Fernando López, José L Mascareñas.

Abstract

The first highly enantioselective intermolecular (4 + 2) cycloaddition between allenes and dienes is reported. The reaction provides good yields of optically active cyclohexenes featuring diverse substitution patterns and up to three stereocenters. Key to the success of the process is the use of newly designed axially chiral N-heterocyclic carbene-gold catalysts.

Entities: Chemical Disease

Year: 2012 PMID： 22892048 DOI： 10.1021/ja3065446

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

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Cited

18 in total

1. Asymmetric gold-catalyzed lactonizations in water at room temperature.

Authors: Sachin Handa; Daniel J Lippincott; Donald H Aue; Bruce H Lipshutz
Journal: Angew Chem Int Ed Engl Date: 2014-08-14 Impact factor: 15.336

2. Synthesis of Chiral Bifunctional NHC Ligands and Survey of Their Utilities in Asymmetric Gold Catalysis.

Authors: Jun-Qi Zhang; Yunkui Liu; Xing-Wang Wang; Liming Zhang
Journal: Organometallics Date: 2019-10-28 Impact factor: 3.876

3. Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes.

Authors: Dimitri A Khrakovsky; Chuanzhou Tao; Miles W Johnson; Richard T Thornbury; Sophia L Shevick; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2016-04-20 Impact factor: 15.336

4. α-Aryl-substituted allenamides in an imino-Nazarov cyclization cascade catalyzed by Au(I).

Authors: Zhi-Xiong Ma; Shuzhong He; Wangze Song; Richard P Hsung
Journal: Org Lett Date: 2012-11-02 Impact factor: 6.005

Review 5. Allenamides: a powerful and versatile building block in organic synthesis.

Authors: Ting Lu; Zhenjie Lu; Zhi-Xiong Ma; Yu Zhang; Richard P Hsung
Journal: Chem Rev Date: 2013-04-04 Impact factor: 60.622

6. Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization.

Authors: Zachary L Niemeyer; Suresh Pindi; Dimitri A Khrakovsky; Christian N Kuzniewski; Cynthia M Hong; Leo A Joyce; Matthew S Sigman; F Dean Toste
Journal: J Am Chem Soc Date: 2017-09-08 Impact factor: 15.419

Axially chiral triazoloisoquinolin-3-ylidene ligands in gold(I)-catalyzed asymmetric intermolecular (4 + 2) cycloadditions of allenamides and dienes.

1. Asymmetric gold-catalyzed lactonizations in water at room temperature.

2. Synthesis of Chiral Bifunctional NHC Ligands and Survey of Their Utilities in Asymmetric Gold Catalysis.

3. Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes.

4. α-Aryl-substituted allenamides in an imino-Nazarov cyclization cascade catalyzed by Au(I).

Review 5. Allenamides: a powerful and versatile building block in organic synthesis.

6. Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization.

7. Development of catalysts and ligands for enantioselective gold catalysis.

Review 8. Gold(I)-catalyzed enantioselective cycloaddition reactions.

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

10. Anatomy of gold catalysts: facts and myths.