Literature DB >> 16671795

Enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by bifunctional tridentate bis(oxazoline)-Zn(II) complex.

Shao-Feng Lu1, Da-Ming Du, Jiaxi Xu.   

Abstract

[reaction: see text] A more practical and efficient catalytic asymmetric Friedel-Crafts alkylation of indoles with nitroalkenes using bifunctional tridentate bis(oxazoline)-Zn(OTf)(2) as catalyst has been developed. Various types of the nitroalkylated indoles were obtained in excellent yields (85-99%) and high enantioselectivities (up to 98% ee).

Entities:  

Year:  2006        PMID： 16671795     DOI： 10.1021/ol060586f

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


  6 in total

1.  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

2.  Zn-catalyzed enantio- and diastereoselective formal [4 + 2] cycloaddition involving two electron-deficient partners: asymmetric synthesis of piperidines from 1-azadienes and nitro-alkenes.

Authors:  John C K Chu; Derek M Dalton; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2015-03-30       Impact factor: 15.419

3.  Second-generation DBFOX ligands for the synthesis of beta-substituted alpha-amino acids via enantioselective radical conjugate additions.

Authors:  Biplab Banerjee; Steven G Capps; Junghoon Kang; Joshua W Robinson; Steven L Castle
Journal:  J Org Chem       Date:  2008-10-24       Impact factor: 4.354

4.  Synthesis of new C2- symmetric fluoren-9-ylidene malonate derived bis(oxazoline) ligands and their application in Friedel-Crafts reactions.

Authors:  Jing Li; Hong-Liang Chen; Lei Liu; Bin Fu
Journal:  Molecules       Date:  2010-11-26       Impact factor: 4.411

5.  Rose bengal as photocatalyst: visible light-mediated Friedel-Crafts alkylation of indoles with nitroalkenes in water.

Authors:  Zong-Yi Yu; Jing-Nan Zhao; Fan Yang; Xiao-Fei Tang; Yu-Feng Wu; Cun-Fei Ma; Bo Song; Lei Yun; Qing-Wei Meng
Journal:  RSC Adv       Date:  2020-01-29       Impact factor: 4.036

6.  Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans.

Authors:  Jiahuan Peng; Da-Ming Du
Journal:  Beilstein J Org Chem       Date:  2013-06-24       Impact factor: 2.883
  6 in total

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