期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 363, 期 7, 页码 1955-1962出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100029
关键词
Organocatalysis; Asymmetric phase-transfer catalysis; Bifunctional catalysis; Heterofunctionalization; Organofluorine chemistry
资金
- Austrian Science Funds (FWF) [P30237, P31784]
- European Union through the EFRE INTERREG IV ETC-ATCZ program [M00146]
- Austrian Science Fund (FWF) [P30237, P31784] Funding Source: Austrian Science Fund (FWF)
In this study, chiral 3,3-disubstituted isoindolinones were synthesized using ammonium salt catalysis, yielding a variety of differently substituted CF3S- and RS-derivatives with high enantioselectivities. Additionally, a racemic synthesis of F-containing products was achieved for the first time, producing a stable alpha-F-alpha-amino acid derivative.
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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