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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