Literature DB >> 22773055

The highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids.

Jingchao Feng1, Wenjin Yan, Dong Wang, Peng Li, Quantao Sun, Rui Wang.   

Abstract

The first asymmetric aza-Friedel-Crafts reaction of indoles and pyrroles with isatin-derived N-Boc ketimines catalyzed by chiral phosphoric acids is reported. In general, derivatives of substituted 3-amino-2-oxindoles were obtained with excellent enantioselectivities and high yields.

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Year:  2012        PMID： 22773055     DOI： 10.1039/c2cc33200k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  9 in total

1.  Controlling Regioselectivity in the Enantioselective N-Alkylation of Indole Analogues Catalyzed by Dinuclear Zinc-ProPhenol.

Authors:  Barry M Trost; Elumalai Gnanamani; Chao-I Joey Hung
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-19       Impact factor: 15.336

2.  Enantioselective synthesis of α-tetrasubstituted (3-indolizinyl) (diaryl)methanamines via chiral phosphoric acid catalysis.

Authors:  Jialing Zhong; Rihuang Pan; Xufeng Lin
Journal:  RSC Adv       Date:  2022-07-15       Impact factor: 4.036

3.  Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers.

Authors:  Fang-Le Hu; Yin Wei; Min Shi; Suresh Pindi; Guigen Li
Journal:  Org Biomol Chem       Date:  2013-02-13       Impact factor: 3.876

4.  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

5.  Selecting Chiral BINOL-Derived Phosphoric Acid Catalysts: General Model To Identify Steric Features Essential for Enantioselectivity.

Authors:  Jolene P Reid; Jonathan M Goodman
Journal:  Chemistry       Date:  2017-09-14       Impact factor: 5.236

6.  Phosphoric acid-catalyzed atroposelective construction of axially chiral arylpyrroles.

Authors:  Lei Zhang; Shao-Hua Xiang; Jun Joelle Wang; Jian Xiao; Jun-Qi Wang; Bin Tan
Journal:  Nat Commun       Date:  2019-02-04       Impact factor: 14.919

7.  Enantioselective Michael addition/iminium ion cyclization cascades of tryptamine-derived ureas.

Authors:  Isabelle Aillaud; David M Barber; Amber L Thompson; Darren J Dixon
Journal:  Org Lett       Date:  2013-05-30       Impact factor: 6.005

8.  Chiral Brønsted acid-catalyzed enantioselective Friedel-Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ.

Authors:  Azusa Kondoh; Yusuke Ota; Takazumi Komuro; Fuyuki Egawa; Kyohei Kanomata; Masahiro Terada
Journal:  Chem Sci       Date:  2015-10-30       Impact factor: 9.825

9.  Lewis Acid-Catalyzed Enantioselective Friedel-Crafts Alkylation of Pyrrole in Water.

Authors:  Jianan Sun; Yang Gui; Yekai Huang; Jindong Li; Zhenggen Zha; Yu Yang; Zhiyong Wang
Journal:  ACS Omega       Date:  2020-05-11
  9 in total

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