Literature DB >> 19746916

Highly enantioselective alkylation reaction of enamides by Brønsted-acid catalysis.

Qi-Xiang Guo1, Yun-Gui Peng, Jin-Wei Zhang, Liu Song, Zhang Feng, Liu-Zhu Gong.   

Abstract

The H8-BINOL-derived, phosphoric acid catalyzed, highly enatioselective alkylation reaction of enamides with indolyl alcohols has been described. A phosphoric acid derived from H8-BINOL enabled an asymmetric alpha-alkylation of enamides with indolyl alcohols to give beta-aryl 3-(3-indolyl)propanones in high yields (up to 96%) and with excellent enantioselectivity (up to 96% ee).

Entities:  

Year:  2009        PMID： 19746916     DOI： 10.1021/ol901892s

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  Synthesis and Preliminary Biological Study of Bisindolylmethanes Accessed by an Acid-Catalyzed Hydroarylation of Vinylindoles.

Authors:  Tejas P Pathak; Jaroslaw G Osiak; Rachel M Vaden; Bryan E Welm; Matthew S Sigman
Journal:  Tetrahedron       Date:  2012-07-01       Impact factor: 2.457

2.  Chiral Brønsted base-promoted nitroalkane alkylation: enantioselective synthesis of sec-alkyl-3-substituted indoles.

Authors:  Mark C Dobish; Jeffrey N Johnston
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

3.  Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols.

Authors:  Eric D Nacsa; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2018-02-22       Impact factor: 15.419

4.  The progression of chiral anions from concepts to applications in asymmetric catalysis.

Authors:  Robert J Phipps; Gregory L Hamilton; F Dean Toste
Journal:  Nat Chem       Date:  2012-07-24       Impact factor: 24.427

Review 5.  Asymmetric ion-pairing catalysis.

Authors:  Katrien Brak; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

6.  Chiral Brønsted Acid-Catalyzed Enantioselective α-Amidoalkylation Reactions: A Joint Experimental and Predictive Study.

Authors:  Eider Aranzamendi; Sonia Arrasate; Nuria Sotomayor; Humberto González-Díaz; Esther Lete
Journal:  ChemistryOpen       Date:  2016-11-23       Impact factor: 2.911

7.  Development of an imidazole salt catalytic system for the preparation of bis(indolyl)methanes and bis(naphthyl)methane.

Authors:  Xu Wang; Courtney C Aldrich
Journal:  PLoS One       Date:  2019-04-25       Impact factor: 3.240

8.  Inner filter effect between upconversion nanoparticles and Fe(ii)-1,10-phenanthroline complex for the detection of Sn(ii) and ascorbic acid (AA).

Authors:  Haining Song; Yifei Zhou; Zexin Li; Haifeng Zhou; Fenglei Sun; Zhenlei Yuan; Peng Guo; Guangjun Zhou; Xiaoqiang Yu; Jifan Hu
Journal:  RSC Adv       Date:  2021-05-11       Impact factor: 4.036

9.  Enantioselective and diastereoselective azo-coupling/iminium-cyclizations: a unified strategy for the total syntheses of (-)-psychotriasine and (+)-pestalazine B.

Authors:  Qi Li; Tingting Xia; Licheng Yao; Haiteng Deng; Xuebin Liao
Journal:  Chem Sci       Date:  2015-05-05       Impact factor: 9.825
  9 in total

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