| 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. |
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@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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