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Literature DB >> 21141997

Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.

Fenghai Guo¹, Leah C Konkol, Regan J Thomson.

Abstract

A method for the enantioselective synthesis of biphenols from readily prepared 1,4-diketones is reported. Key to the success of this method is the highly selective transfer of central to axial chirality during a double aromatization event triggered by BF(3)·OEt(2). On the basis of X-ray crystallographic data, a stereochemical model for this chirality exchange process is put forth.

Entities: Chemical

Mesh：

Substances：
Ketones
Phenols

Year: 2010 PMID： 21141997 PMCID： PMC3073418 DOI： 10.1021/ja108717r

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

23 in total

1. Catalyzed Asymmetric Arylation Reactions.

Authors: Carsten Bolm; Jens P. Hildebrand; Kilian Muñiz; Nina Hermanns
Journal: Angew Chem Int Ed Engl Date: 2001-09-17 Impact factor: 15.336

2. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

Authors: Jwanro Hassan; Marc Sévignon; Christel Gozzi; Emmanuelle Schulz; Marc Lemaire
Journal: Chem Rev Date: 2002-05 Impact factor: 60.622

3. A new entry of nucleophiles in rhodium-catalyzed asymmetric 1,4-addition reactions: addition of organozinc reagents for the synthesis of 2-aryl-4-piperidones.

Authors: Ryo Shintani; Norihito Tokunaga; Hidenori Doi; Tamio Hayashi
Journal: J Am Chem Soc Date: 2004-05-26 Impact factor: 15.419

4. A rationally designed universal catalyst for Suzuki-Miyaura coupling processes.

Authors: Shawn D Walker; Timothy E Barder; Joseph R Martinelli; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2004-03-26 Impact factor: 15.336

5. Synthetic strategy: Moving backwards in new ways.

Authors: Nathan Collett; Rich G Carter
Journal: Nat Chem Date: 2010-08 Impact factor: 24.427

6. Atroposelective synthesis of axially chiral biaryl compounds.

Authors: Gerhard Bringmann; Anne J Price Mortimer; Paul A Keller; Mary J Gresser; James Garner; Matthias Breuning
Journal: Angew Chem Int Ed Engl Date: 2005-08-26 Impact factor: 15.336

7. Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers.

Authors: Christopher T Avetta; Leah C Konkol; Carla N Taylor; Karen C Dugan; Charlotte L Stern; Regan J Thomson
Journal: Org Lett Date: 2008-12-18 Impact factor: 6.005

8. Chirality exchange from sp3 central chirality to axial chirality: benzannulation of optically active diaryl-2,2-dichlorocyclopropylmethanols to axially chiral alpha-arylnaphthalenes.

Authors: Yoshinori Nishii; Kazunori Wakasugi; Keisuke Koga; Yoo Tanabe
Journal: J Am Chem Soc Date: 2004-05-05 Impact factor: 15.419

9. Scalable total synthesis and biological evaluation of haouamine A and its atropisomer.

Authors: Noah Z Burns; Irina N Krylova; Rami N Hannoush; Phil S Baran
Journal: J Am Chem Soc Date: 2009-07-08 Impact factor: 15.419

10. Controlling axial conformation in 2-arylpyridines and 1-arylisoquinolines: application to the asymmetric synthesis of QUINAP by dynamic thermodynamic resolution.

Authors: Jonathan Clayden; Stephen P Fletcher; Joseph J W McDouall; Stephen J M Rowbottom
Journal: J Am Chem Soc Date: 2009-04-15 Impact factor: 15.419

15 in total

1. Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

Authors: Xiaowei Wu; Takayuki Iwata; Adam Scharf; Tian Qin; Kyle D Reichl; John A Porco
Journal: J Am Chem Soc Date: 2018-04-25 Impact factor: 15.419

2. Symmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives.

Authors: Jin-Zheng Wang; Jin Zhou; Chang Xu; Hongbin Sun; László Kürti; Qing-Long Xu
Journal: J Am Chem Soc Date: 2016-04-14 Impact factor: 15.419

Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.

1. Catalyzed Asymmetric Arylation Reactions.

2. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

3. A new entry of nucleophiles in rhodium-catalyzed asymmetric 1,4-addition reactions: addition of organozinc reagents for the synthesis of 2-aryl-4-piperidones.

4. A rationally designed universal catalyst for Suzuki-Miyaura coupling processes.

5. Synthetic strategy: Moving backwards in new ways.

6. Atroposelective synthesis of axially chiral biaryl compounds.

7. Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers.

8. Chirality exchange from sp3 central chirality to axial chirality: benzannulation of optically active diaryl-2,2-dichlorocyclopropylmethanols to axially chiral alpha-arylnaphthalenes.

9. Scalable total synthesis and biological evaluation of haouamine A and its atropisomer.

10. Controlling axial conformation in 2-arylpyridines and 1-arylisoquinolines: application to the asymmetric synthesis of QUINAP by dynamic thermodynamic resolution.

1. Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

2. Symmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives.

3. Catalytic enantioselective synthesis of atropisomeric biaryls by a cation-directed O-alkylation.

4. Asymmetric transformations of achiral 2,5-cyclohexadienones.

5. Enantioselective total synthesis and studies into the configurational stability of bismurrayaquinone A.

6. Atropisomerism in the Pharmaceutically Relevant Realm.

7. Oxidative Coupling of Enolates, Enol Silanes and Enamines: Methods and Natural Product Synthesis.

8. Total Synthesis of Propolisbenzofuran B.

9. Crystal structure of 5,5'-di-bromo-3,3'-di-tert-butyl-6,6'-di-methyl-biphenyl-2,2'-diol.

10. Atropselective syntheses of (-) and (+) rugulotrosin A utilizing point-to-axial chirality transfer.