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Literature DB >> 25562811

Enantioselective gold catalyzed dearomative [2+2]-cycloaddition between indoles and allenamides.

Minqiang Jia¹, Magda Monari, Qing-Qing Yang, Marco Bandini.

Abstract

The highly enantioselective synthesis of densely functionalized 2,3-indoline-cyclobutanes by means of chiral gold catalysis is presented. Intermolecular formal [2+2]-cycloaddition reactions between substituted indoles and allenamides enabled direct access to methylenecyclobutane-fused indolines, featuring two consecutive quaternary stereogenic centers with excellent stereochemical control (dr > 20 : 1, ee up to 99%).

Entities: Chemical

Mesh：

Substances：
Amides
Indoles
Gold

Year: 2015 PMID： 25562811 DOI： 10.1039/c4cc08736d

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

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Cited

7 in total

1. Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

Authors: Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal: J Am Chem Soc Date: 2018-11-05 Impact factor: 15.419

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 gold-catalyzed intermolecular [2+2] versus [4+2]-cycloadditions of 3-styrylindoles with N-allenamides: observation of interesting substituent effects.

Authors: Yidong Wang; Peichao Zhang; Yuan Liu; Fei Xia; Junliang Zhang
Journal: Chem Sci Date: 2015-06-23 Impact factor: 9.825

Enantioselective gold catalyzed dearomative [2+2]-cycloaddition between indoles and allenamides.

1. Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

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

3. Enantioselective gold-catalyzed intermolecular [2+2] versus [4+2]-cycloadditions of 3-styrylindoles with N-allenamides: observation of interesting substituent effects.

4. Construction of spirocarbocycles via gold-catalyzed intramolecular dearomatization of naphthols.

5. Allenes and Derivatives in Gold(I)- and Platinum(II)-Catalyzed Formal Cycloadditions.

6. Iridium-Catalyzed Enantioselective Intermolecular Indole C2-Allylation.

7. Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch.