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Beilstein J. Org. Chem. 2018, 14, 593–602, doi:10.3762/bjoc.14.46
Graphical Abstract
Figure 1: Examples of synthetic pharmacologically active chiral 3-substituted isoindolinones.
Scheme 1: Retrosynthetic analysis of NH free chiral 3-substituted isoindolinones (3S)-1 and (3S)-2.
Scheme 2: Synthesis of parent benzamides 6–8.
Figure 2: Esters 12a–e, 13 prepared, isolated yield.
Figure 3: Benzamides 6a–d, 7a–e, 8 prepared, isolated yield.
Figure 4: Phase transfer catalysts (PTC) used in this study.
Scheme 3: Synthesis of isoindolinones 3a–d, 4a–e, 5; isolated yield, de by HPLC and 1H NMR. aAfter flash chro...
Scheme 4: Removal of the chiral auxiliary. Synthesis of isoindolinones 1a–c, 1e, 2; isolated yield, ee by HPL...
Figure 5: ORTEP plot of isoindolinone (2R,3S)-3a (CCDC 1590565) [68].
Scheme 5: Synthesis of pazinaclone analogue (3S)-27.