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Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF3S-, 3-RS-, and 3-F-Substituted Isoindolinones.

Authors
  • Eitzinger, Andreas1
  • Otevrel, Jan1, 2
  • Haider, Victoria1
  • Macchia, Antonio3
  • Massa, Antonio3
  • Faust, Kirill4
  • Spingler, Bernhard5
  • Berkessel, Albrecht6
  • Waser, Mario1
  • 1 Institute of Organic Chemistry Johannes Kepler University Linz Altenbergerstr. 69 4040 Linz Austria. , (Austria)
  • 2 Department of Chemical Drugs Faculty of Pharmacy Masaryk University Palackeho 1946/1 612 00 Brno Czechia.
  • 3 Dipartimento di Chimica e Biologia Università di Salerno Via Giovanni Paolo II, 132 84084 Fisciano SA Italy. , (Italy)
  • 4 Institute of Catalysis Johannes Kepler University Linz Altenbergerstr. 69 4040 Linz Austria. , (Austria)
  • 5 Department of Chemistry University of Zurich Winterthurerstrasse 190 8057 Zurich Switzerland. , (Switzerland)
  • 6 Department of Chemistry Cologne University Greinstrasse 4 50939 Cologne Germany. , (Germany)
Type
Published Article
Journal
Advanced Synthesis & Catalysis
Publisher
Wiley
Publication Date
Mar 29, 2021
Volume
363
Issue
7
Pages
1955–1962
Identifiers
DOI: 10.1002/adsc.202100029
PMID: 33897314
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

We herein report the ammonium salt-catalyzed synthesis of chiral 3,3-disubstituted isoindolinones bearing a heteroatom functionality in the 3-position. A broad variety of differently substituted CF3S- and RS-derivatives were obtained with often high enantioselectivities when using Maruoka's bifunctional chiral ammonium salt catalyst. In addition, a first proof-of-concept for the racemic synthesis of the analogous F-containing products was obtained as well, giving access to one of the rare examples of a fairly stable α-F-α-amino acid derivative. © 2021 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH.

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