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Literature DB >> 26384020

Copper-catalyzed enantioselective 1,6-boration of para-quinone methides and efficient transformation of gem-diarylmethine boronates to triarylmethanes.

Yazhou Lou^1,2, Peng Cao^1,2, Tao Jia^1,2, Yongling Zhang^1,2, Min Wang^1,2, Jian Liao^3,4,5.

Abstract

Presented is the first enantioselective copper-catalyzed 1,6-conjugate addition of bis(pinacolato)diboron to para-quinone methides. The reaction proceeds with excellent yields and good to excellent enantioselectivities, and provides an attractive approach to the construction of optically active gem-diarylmehtine boronic esters. Additionally, the subsequent conversion of the derived potassium trifluoroborates into triarylmethanes with highly enantiospecificity was realized.

Entities: Chemical

Keywords: asymmetric catalysis; boron; copper; cross-coupling; synthetic methods

Mesh：

Substances：

Year: 2015 PMID： 26384020 DOI： 10.1002/anie.201505926

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

24 in total

1. A General Approach to Stereospecific Cross-Coupling Reactions of Nitrogen-Containing Stereocenters.

Authors: Xinghua Ma; Haoran Zhao; Meruyert Binayeva; Glenn Ralph; Mohamed Diane; Shibin Zhao; Chao-Yuan Wang; Mark R Biscoe
Journal: Chem Date: 2020-03-02 Impact factor: 22.804

2. Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles.

Authors: Xinghua Ma; Benjamin Murray; Mark R Biscoe
Journal: Nat Rev Chem Date: 2020-09-24 Impact factor: 34.035

3. Copper(I)-Catalyzed Asymmetric Conjugate 1,6-, 1,8-, and 1,10-Borylation.

Authors: Chang-Yun Shi; Jungmin Eun; Timothy R Newhouse; Liang Yin
Journal: Angew Chem Int Ed Engl Date: 2021-03-18 Impact factor: 15.336

4. Cross-dehydrogenative coupling enables enantioselective access to CF₃-substituted all-carbon quaternary stereocenters.

Authors: Xiaoguang Pan; Zehua Wang; Linglong Kan; Ying Mao; Yasheng Zhu; Lei Liu
Journal: Chem Sci Date: 2020-01-29 Impact factor: 9.825

9. Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents.

Authors: Baosheng Wei; Qianyi Ren; Thomas Bein; Paul Knochel
Journal: Angew Chem Int Ed Engl Date: 2021-03-17 Impact factor: 15.336

10. Size-Induced Inversion of Selectivity in the Acylation of 1,2-Diols.

Authors: Stefanie Mayr; Hendrik Zipse
Journal: Chemistry Date: 2021-11-29 Impact factor: 5.020

Copper-catalyzed enantioselective 1,6-boration of para-quinone methides and efficient transformation of gem-diarylmethine boronates to triarylmethanes.

1. A General Approach to Stereospecific Cross-Coupling Reactions of Nitrogen-Containing Stereocenters.

2. Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles.

3. Copper(I)-Catalyzed Asymmetric Conjugate 1,6-, 1,8-, and 1,10-Borylation.

4. Cross-dehydrogenative coupling enables enantioselective access to CF₃-substituted all-carbon quaternary stereocenters.

5. Copper-Catalyzed Borylative Aromatization of p-Quinone Methides: Enantioselective Synthesis of Dibenzylic Boronates.

6. Development of Enantiospecific Coupling of Secondary and Tertiary Boronic Esters with Aromatic Compounds.

7. Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation.

8. Enantio- and diastereoselective diarylmethylation of 1,3-dicarbonyl compounds.

9. Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents.

10. Size-Induced Inversion of Selectivity in the Acylation of 1,2-Diols.