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


Eitzinger, Andreas; Otevrel, Jan; Haider, Victoria; Macchia, Antonio; Massa, Antonio; Faust, Kirill; Spingler, Bernhard; Berkessel, Albrecht; Waser, Mario (2021). Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF3S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones. Advanced Synthesis & Catalysis, 363(7):1955-1962.

Abstract

We herein report the ammonium saltcatalyzed 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.

Abstract

We herein report the ammonium saltcatalyzed 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.

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Organic Chemistry, General Chemistry, Catalysis
Language:English
Date:29 March 2021
Deposited On:07 Apr 2021 15:20
Last Modified:24 Feb 2024 02:49
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:1615-4150
OA Status:Hybrid
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/adsc.202100029
  • Content: Published Version
  • Licence: Creative Commons: Attribution 4.0 International (CC BY 4.0)