Literature DB >> 19334771

Chiral Brønsted acid-catalyzed enantioselective three-component Povarov reaction.

Hua Liu1, Guillaume Dagousset, Géraldine Masson, Pascal Retailleau, Jieping Zhu.   

Abstract

The three-component Povarov reaction of aldehydes (2), anilines (3), and benzyl N-vinylcarbamate 4 in the presence of 0.1 equiv of chiral phosphoric acid 5 afforded cis-2,4-disubstituted tetrahydroquinolines (1) in good yields and excellent enantiomeric excesses. The shortest synthesis of torcetrapib reported to date, which features this key three-component reaction, is documented.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19334771     DOI： 10.1021/ja900806q

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


  22 in total

Review 1.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2010-10-05

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.  Highly enantioselective trapping of zwitterionic intermediates by imines.

Authors:  Huang Qiu; Ming Li; Li-Qin Jiang; Feng-Ping Lv; Li Zan; Chang-Wei Zhai; Michael P Doyle; Wen-Hao Hu
Journal:  Nat Chem       Date:  2012-07-29       Impact factor: 24.427

4.  Chiral sulfinamidourea and strong Brønsted acid-cocatalyzed enantioselective Povarov reaction to access tetrahydroquinolines.

Authors:  Hao Xu; Hu Zhang; Eric N Jacobsen
Journal:  Nat Protoc       Date:  2014-07-10       Impact factor: 13.491

5.  Chiral phosphoric acid catalyzed addition of dihydropyrans to N-acyl imines: stereocontrolled access to enantioenriched spirocyclic oxazoletetrahydropyrans with three contiguous stereocenters.

Authors:  Guilong Li; Matthew J Kaplan; Lukasz Wojtas; Jon C Antilla
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

6.  N-triflylthiophosphoramide catalyzed enantioselective Mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones.

Authors:  Cheol Hong Cheon; Hisashi Yamamoto
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

7.  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

8.  Asymmetric cooperative catalysis of strong Brønsted acid-promoted reactions using chiral ureas.

Authors:  Hao Xu; Stephan J Zuend; Matthew G Woll; Ye Tao; Eric N Jacobsen
Journal:  Science       Date:  2010-02-19       Impact factor: 47.728

9.  Application of a catalytic asymmetric Povarov reaction using chiral ureas to the synthesis of a tetrahydroquinoline library.

Authors:  Baudouin Gerard; Morgan Welzel O'Shea; Etienne Donckele; Sarathy Kesavan; Lakshmi B Akella; Hao Xu; Eric N Jacobsen; Lisa A Marcaurelle
Journal:  ACS Comb Sci       Date:  2012-10-22       Impact factor: 3.784

10.  Transformation of N, N-Dimethylaniline N-Oxides into Diverse Tetrahydroquinoline Scaffolds via Formal Povarov Reactions.

Authors:  Timothy S Bush; Glenn P A Yap; William J Chain
Journal:  Org Lett       Date:  2018-08-15       Impact factor: 6.005
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.