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

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EITZINGER A. OTEVŘEL Jan HAIDER V. MACCHIA A. MASSA A. FAUST K. SPINGLER B. BERKESSEL A. WASER M.

Rok publikování 2021
Druh Článek v odborném periodiku
Časopis / Zdroj ADVANCED SYNTHESIS & CATALYSIS
Fakulta / Pracoviště MU

Farmaceutická fakulta

Citace
www https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/adsc.202100029
Doi http://dx.doi.org/10.1002/adsc.202100029
Klíčová slova Organocatalysis; Asymmetric phase-transfer catalysis; Bifunctional catalysis; Heterofunctionalization; Organofluorine chemistry
Popis 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 alpha-F-alpha-amino acid derivative.

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