Literature DB >> 21082787

SPINOL-derived phosphoric acids: synthesis and application in enantioselective Friedel-Crafts reaction of indoles with imines.

Fangxi Xu1, Dan Huang, Chao Han, Wei Shen, Xufeng Lin, Yanguang Wang.   

Abstract

A new class of chiral phosphoric acids with spirobiindane as scaffold were conveniently synthesized from (S)-1,1'-spirobiindane-7,7'-diol ((S)-SPINOL) and employed to catalyze the asymmetric Friedel-Crafts reaction of indoles with imines to afford 3-indolyl methanamines. High yields (68-97%) and excellent enantioselectivities (up to 99% ee) were obtained.

Entities:  

Year:  2010        PMID： 21082787     DOI： 10.1021/jo101640z

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  9 in total

1.  Asymmetric spiroacetalization catalysed by confined Brønsted acids.

Authors:  Ilija Čorić; Benjamin List
Journal:  Nature       Date:  2012-03-14       Impact factor: 49.962

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.  Phosphothreonine as a catalytic residue in peptide-mediated asymmetric transfer hydrogenations of 8-aminoquinolines.

Authors:  Christopher R Shugrue; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-05       Impact factor: 15.336

4.  Catalytic asymmetric total syntheses of myrtucommuacetalone, myrtucommuacetalone B, and callistrilones A, C, D and E.

Authors:  Min-Jing Cheng; Jia-Qing Cao; Xin-Yi Yang; Li-Ping Zhong; Li-Jun Hu; Xi Lu; Bao-Long Hou; Ya-Jian Hu; Ying Wang; Xue-Fu You; Lei Wang; Wen-Cai Ye; Chuang-Chuang Li
Journal:  Chem Sci       Date:  2017-11-27       Impact factor: 9.825

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.  Rigid 3D-spiro chromanone as a crux for efficient antimicrobial agents: synthesis, biological and computational evaluation.

Authors:  F H Elghareeb; E M Kandil; M Abou-Elzahab; M Abdelmoteleb; M A Abozeid
Journal:  RSC Adv       Date:  2021-06-16       Impact factor: 4.036

7.  Gold and BINOL-phosphoric acid catalyzed enantioselective hydroamination/N-sulfonyliminium cyclization cascade.

Authors:  Alex W Gregory; Pavol Jakubec; Paul Turner; Darren J Dixon
Journal:  Org Lett       Date:  2013-08-28       Impact factor: 6.005

8.  Efficient synthesis of dihydropyrimidinones via a three-component Biginelli-type reaction of urea, alkylaldehyde and arylaldehyde.

Authors:  Haijun Qu; Xuejian Li; Fan Mo; Xufeng Lin
Journal:  Beilstein J Org Chem       Date:  2013-12-11       Impact factor: 2.883

9.  Highly efficient enantioselective liquid-liquid extraction of 1,2-amino-alcohols using SPINOL based phosphoric acid hosts.

Authors:  Erik B Pinxterhuis; Jean-Baptiste Gualtierotti; Hero J Heeres; Johannes G de Vries; Ben L Feringa
Journal:  Chem Sci       Date:  2017-07-21       Impact factor: 9.825
  9 in total

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