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Literature DB >> 23634801

Construction of a chiral quaternary carbon center by catalytic asymmetric alkylation of 2-arylcyclohexanones under phase-transfer conditions.

Taichi Kano¹, Yumi Hayashi, Keiji Maruoka.

Abstract

In this paper, we present an asymmetric alkylation of modified 2-arylcyclohexanones that employs a novel chiral ammonium bromide as a phase-transfer catalyst and an achiral auxiliary as a controller to improve the enantioselectivity to afford optically enriched products having a chiral quaternary carbon center.

Entities: Chemical

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Year: 2013 PMID： 23634801 DOI： 10.1021/ja403340r

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

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Cited

12 in total

Review 1. Direct Asymmetric Alkylation of Ketones: Still Unconquered.

Authors: Rafael Cano; Armen Zakarian; Gerard P McGlacken
Journal: Angew Chem Int Ed Engl Date: 2017-06-27 Impact factor: 15.336

2. Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.

Authors: Nathan J Adamson; Katherine C E Wilbur; Steven J Malcolmson
Journal: J Am Chem Soc Date: 2018-02-20 Impact factor: 15.419

3. Direct asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid.

Authors: Xiaoyu Yang; F Dean Toste
Journal: J Am Chem Soc Date: 2015-02-26 Impact factor: 15.419

4. Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.

Authors: Yujing Zhou; Jeffrey S Bandar; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2017-06-06 Impact factor: 15.419

5. Diastereo- and enantioselective iridium-catalyzed allylation of cyclic ketone enolates: synergetic effect of ligands and barium enolates.

Authors: Wenyong Chen; Ming Chen; John F Hartwig
Journal: J Am Chem Soc Date: 2014-10-30 Impact factor: 15.419

6. Sterically Demanding Unsymmetrical Diaryl-λ(3)-iodanes for Electrophilic Pentafluorophenylation and an Approach to α-Pentafluorophenyl Carbonyl Compounds with an All-Carbon Stereocenter.

Authors: Kohei Matsuzaki; Kenta Okuyama; Etsuko Tokunaga; Motoo Shiro; Norio Shibata
Journal: ChemistryOpen Date: 2014-09-17 Impact factor: 2.911

Construction of a chiral quaternary carbon center by catalytic asymmetric alkylation of 2-arylcyclohexanones under phase-transfer conditions.

Review 1. Direct Asymmetric Alkylation of Ketones: Still Unconquered.

2. Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.

3. Direct asymmetric amination of α-branched cyclic ketones catalyzed by a chiral phosphoric acid.

4. Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.

5. Diastereo- and enantioselective iridium-catalyzed allylation of cyclic ketone enolates: synergetic effect of ligands and barium enolates.

6. Sterically Demanding Unsymmetrical Diaryl-λ(3)-iodanes for Electrophilic Pentafluorophenylation and an Approach to α-Pentafluorophenyl Carbonyl Compounds with an All-Carbon Stereocenter.

7. Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid.

8. Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes.

9. Asymmetric benzylic C(sp³)-H acylation via dual nickel and photoredox catalysis.

Review 10. Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry.