Literature DB >> 30379081

Revisiting the CuII-Catalyzed Asymmetric Friedel-Crafts Reaction of Indole with Trifluoropyruvate.

Thien Phuc Le1, Kazuyuki Higashita1, Shinji Tanaka1, Masahiro Yoshimura2, Masato Kitamura1.   

Abstract

A CuII complex of bisamidine ligand L S catalyzes the Friedel-Crafts (FC) reaction of indole with trifluoropyruvate with high generality, yielding the highly enantiomerically enriched FC adduct. Electron-rich indoles have high reactivity due to a dual activation mechanism showing second-order kinetics for CuII, whereas indoles with a soft substituent at C(4) proceed at a rate that is three orders of magnitude lower via a coordination mechanism, which reverses the sense of enantioselectivity.

Entities:  

Year:  2018        PMID： 30379081     DOI： 10.1021/acs.orglett.8b03086

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


  2 in total

1.  Synthesis of α-CF3-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors.

Authors:  Michael Winter; Kirill Faust; Markus Himmelsbach; Mario Waser
Journal:  Org Biomol Chem       Date:  2019-06-12       Impact factor: 3.876

2.  Pd-Catalyzed Allylation of Imines to Access α-CF3-Substituted α-Amino Acid Derivatives.

Authors:  Michael Winter; Hyunwoo Kim; Mario Waser
Journal:  European J Org Chem       Date:  2019-10-09
  2 in total

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