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

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.

SUBMITTER: Eitzinger A

PROVIDER: S-EPMC8050839 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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

Eitzinger Andreas A Otevrel Jan J Haider Victoria V Macchia Antonio A Massa Antonio A Faust Kirill K Spingler Bernhard B Berkessel Albrecht A Waser Mario M

Advanced synthesis & catalysis 20210217 7

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 ...[more]

PMID: 33897314

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