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

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 bif...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-03, Vol.363 (7), p.1955-1962
Main Authors: Eitzinger, Andreas, Otevrel, Jan, Haider, Victoria, Macchia, Antonio, Massa, Antonio, Faust, Kirill, Spingler, Bernhard, Berkessel, Albrecht, Waser, Mario
Format: Article
Language:English
Subjects:
Amino acids
Asymmetric phase-transfer catalysis
Bifunctional catalysis
Chemical synthesis
Enantiomers
Heterofunctionalization
Organocatalysis
Organofluorine chemistry
Substitutes
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100029