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Literature DB >> 23463273

Chiral aryl iodide catalysts for the enantioselective synthesis of para-quinols.

Abstract

Molecular modelling of an iodine(III) phenoxide was used as a starting point in the design of chiral aryl iodide catalysts for stereoselective oxidative dearomatization reactions. Using this approach, catalysts derived from 8-iodotetralone and tartaric acid were constructed and used to synthesize enantioenriched para-quinols from phenols.

Entities: Chemical

Year: 2013 PMID： 23463273 DOI： 10.1039/c3cc00013c

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

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Cited

11 in total

1. Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

Authors: Andrew M Harned
Journal: Tetrahedron Lett Date: 2014-08-20 Impact factor: 2.415

2. Synthetic utility of one-pot chemoenzymatic reaction sequences.

Authors: Tyler J Doyon; Alison R H Narayan
Journal: Synlett Date: 2019-06-06 Impact factor: 2.454

3. Structural basis for selectivity in flavin-dependent monooxygenase-catalyzed oxidative dearomatization.

Authors: Attabey Rodríguez Benítez; Sara Tweedy; Summer A Baker Dockrey; April L Lukowski; Troy Wymore; Dheeraj Khare; Charles L Brooks; Bruce A Palfey; Janet L Smith; Alison R H Narayan
Journal: ACS Catal Date: 2019-03-25 Impact factor: 13.084

4. Photocatalytic Oxidative Dearomatization of Orcinaldehyde Derivatives.

Authors: Summer A Baker Dockrey; Alison R H Narayan
Journal: Org Lett Date: 2020-04-15 Impact factor: 6.005

5. Whole-cell biocatalysis platform for gram-scale oxidative dearomatization of phenols.

Authors: Summer A Baker Dockrey; Tyler J Doyon; Jonathan C Perkins; Alison R H Narayan
Journal: Chem Biol Drug Des Date: 2018-11-28 Impact factor: 2.817

6. Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis.

Authors: Banruo Huang; Ying He; Mark D Levin; Jaime A S Coelho; Robert G Bergman; F Dean Toste
Journal: Adv Synth Catal Date: 2019-09-06 Impact factor: 5.837

Chiral aryl iodide catalysts for the enantioselective synthesis of para-quinols.

1. Asymmetric oxidative dearomatizations promoted by hypervalent iodine(III) reagents: an opportunity for rational catalyst design?

2. Synthetic utility of one-pot chemoenzymatic reaction sequences.

3. Structural basis for selectivity in flavin-dependent monooxygenase-catalyzed oxidative dearomatization.

4. Photocatalytic Oxidative Dearomatization of Orcinaldehyde Derivatives.

5. Whole-cell biocatalysis platform for gram-scale oxidative dearomatization of phenols.

6. Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis.

7. Positioning-Group-Enabled Biocatalytic Oxidative Dearomatization.

8. Biocatalytic site- and enantioselective oxidative dearomatization of phenols.

Review 9. Recent discoveries on the structure of iodine(iii) reagents and their use in cross-nucleophile coupling.

10. Catalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives.