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

J 2021

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

EITZINGER, A., Jan OTEVŘEL, V. HAIDER, A. MACCHIA, A. MASSA et. al.

Základní údaje

Originální název

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

Autoři

EITZINGER, A., Jan OTEVŘEL (203 Česká republika, domácí), V. HAIDER, A. MACCHIA, A. MASSA, K. FAUST, B. SPINGLER, A. BERKESSEL a M. WASER (garant)

Vydání

ADVANCED SYNTHESIS & CATALYSIS, WEINHEIM, WILEY-V C H VERLAG GMBH, 2021, 1615-4150

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30104 Pharmacology and pharmacy

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 5.981

Kód RIV

RIV/00216224:14160/21:00121318

Organizační jednotka

Farmaceutická fakulta

DOI

http://dx.doi.org/10.1002/adsc.202100029

UT WoS

000618751200001

Klíčová slova anglicky

Organocatalysis; Asymmetric phase-transfer catalysis; Bifunctional catalysis; Heterofunctionalization; Organofluorine chemistry

Štítky

rivok, ÚChL

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 30. 3. 2021 13:29, Mgr. Hana Hurtová

Anotace

V originále

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.

Citovat

EITZINGER, A., Jan OTEVŘEL, V. HAIDER, A. MACCHIA, A. MASSA, K. FAUST, B. SPINGLER, A. BERKESSEL a M. WASER. Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF3S-, 3-RS-, and 3-F-Substituted Isoindolinones. ADVANCED SYNTHESIS & CATALYSIS. WEINHEIM: WILEY-V C H VERLAG GMBH, 2021, roč. 363, č. 363, s. 1955-1963. ISSN 1615-4150. Dostupné z: https://dx.doi.org/10.1002/adsc.202100029.

@article{1756556,
   author = {Eitzinger, A. and Otevřel, Jan and Haider, V. and Macchia, A. and Massa, A. and Faust, K. and Spingler, B. and Berkessel, A. and Waser, M.},
   article_location = {WEINHEIM},
   article_number = {363},
   doi = {http://dx.doi.org/10.1002/adsc.202100029},
   keywords = {Organocatalysis; Asymmetric phase-transfer catalysis; Bifunctional catalysis; Heterofunctionalization; Organofluorine chemistry},
   language = {eng},
   issn = {1615-4150},
   journal = {ADVANCED SYNTHESIS & CATALYSIS},
   title = {Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF3S-, 3-RS-, and 3-F-Substituted Isoindolinones},
   url = {https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/adsc.202100029},
   volume = {363},
   year = {2021}
}

TY  - JOUR
ID  - 1756556
AU  - Eitzinger, A. - Otevřel, Jan - Haider, V. - Macchia, A. - Massa, A. - Faust, K. - Spingler, B. - Berkessel, A. - Waser, M.
PY  - 2021
TI  - Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF3S-, 3-RS-, and 3-F-Substituted Isoindolinones
JF  - ADVANCED SYNTHESIS & CATALYSIS
VL  - 363
IS  - 363
SP  - 1955-1963
EP  - 1955-1963
PB  - WILEY-V C H VERLAG GMBH
SN  - 16154150
KW  - Organocatalysis
KW  - Asymmetric phase-transfer catalysis
KW  - Bifunctional catalysis
KW  - Heterofunctionalization
KW  - Organofluorine chemistry
UR  - https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/adsc.202100029
N2  - 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.
ER  -

EITZINGER, A., Jan OTEVŘEL, V. HAIDER, A. MACCHIA, A. MASSA, K. FAUST, B. SPINGLER, A. BERKESSEL a M. WASER. Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF3S-, 3-RS-, and 3-F-Substituted Isoindolinones. \textit{ADVANCED SYNTHESIS \&{}amp; CATALYSIS}. WEINHEIM: WILEY-V C H VERLAG GMBH, 2021, roč.~363, č.~363, s.~1955-1963. ISSN~1615-4150. Dostupné z: https://dx.doi.org/10.1002/adsc.202100029.

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