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.

Basic information

Original name

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

Authors

EITZINGER, A., Jan OTEVŘEL (203 Czech Republic, belonging to the institution), V. HAIDER, A. MACCHIA, A. MASSA, K. FAUST, B. SPINGLER, A. BERKESSEL and M. WASER (guarantor)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 5.981

RIV identification code

RIV/00216224:14160/21:00121318

Organization unit

Faculty of Pharmacy

DOI

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

UT WoS

000618751200001

Keywords in English

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

Abstract

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 and 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, vol. 363, No 363, p. 1955-1963. ISSN 1615-4150. Available from: 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 and 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, vol.~363, No~363, p.~1955-1963. ISSN~1615-4150. Available from: https://dx.doi.org/10.1002/adsc.202100029.

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