Literature DB >> 20205477

Desymmetrization of cyclohexadienones via Brønsted acid-catalyzed enantioselective oxo-Michael reaction.

Qing Gu1, Zi-Qiang Rong, Chao Zheng, Shu-Li You.   

Abstract

Desymmetrization of cyclohexadienones via enantioselective oxo-Michael reaction catalyzed by chiral phosphoric acid to afford highly enantioenriched 1,4-dioxane and tetrahydrofuran derivatives in excellent yields has been realized. The newly established methodology allows the facile enantioselective synthesis of cleroindicins C, D, and F.

Entities:  

Year:  2010        PMID： 20205477     DOI： 10.1021/ja100207s

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


  18 in total

1.  Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Chem Sci       Date:  2013-07-01       Impact factor: 9.825

2.  An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

Authors:  David M Rubush; Michelle A Morges; Barbara J Rose; Douglas H Thamm; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419

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

Authors:  Kyle A Kalstabakken; Andrew M Harned
Journal:  Tetrahedron       Date:  2014-12-23       Impact factor: 2.457

4.  An organocascade kinetic resolution.

Authors:  Patrick G McGarraugh; Stacey E Brenner-Moyer
Journal:  Org Lett       Date:  2011-11-15       Impact factor: 6.005

Review 5.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

6.  Chiral phosphoric acid catalyzed peroxidation of imines.

Authors:  Wenhua Zheng; Lukasz Wojtas; Jon C Antilla
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-03       Impact factor: 15.336

7.  Convergent total synthesis of (+)-calcipotriol: A scalable, modular approach to vitamin D analogs.

Authors:  Jieyu Gu; Kevin X Rodriguez; Yuzuru Kanda; Shenghua Yang; Michal Ociepa; Henrik Wilke; Arteen V Abrishami; Lars Jørgensen; Tine Skak-Nielsen; Jason S Chen; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2022-04-27       Impact factor: 12.779

8.  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

9.  Enantioselective desymmetrization of prochiral cyclohexanones by organocatalytic intramolecular Michael additions to α,β-unsaturated esters.

Authors:  Adam D Gammack Yamagata; Swarup Datta; Kelvin E Jackson; Linus Stegbauer; Robert S Paton; Darren J Dixon
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-27       Impact factor: 15.336

10.  Enantioselective desymmetrization of cyclohexadienones via an intramolecular Rauhut-Currier reaction of allenoates.

Authors:  Weijun Yao; Xiaowei Dou; Shan Wen; Ji'en Wu; Jagadese J Vittal; Yixin Lu
Journal:  Nat Commun       Date:  2016-10-04       Impact factor: 14.919
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