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A Convenient 5-exo-dig Cyclization Route to Diastereomerically Pure Methyl (2S)-2-(1-benzyl-3-oxo-1,3-dihydro-2H-isoindol-2-yl)-3-methylbutanoate
- Source :
- Chemistry of Heterocyclic Compounds. 56:1370-1374
- Publication Year :
- 2020
- Publisher :
- Springer Science and Business Media LLC, 2020.
-
Abstract
- A robust method toward the synthesis of diastereomerically pure methyl (2S)-2-(1-benzyl-3-oxo-1,3-dihydro-2H-isoindol-2-yl)-3-methylbutanoate has been described. The key reactions in the synthesis are: HATU-mediated coupling, Pd-catalyzed Sonogashira coupling, base-mediated 5-exo-dig cyclization, and catalytic hydrogenation. The diastereomeric mixture is subjected to trituration with heptane to furnish both diastereomers in moderate yields. The relative stereochemistry was confirmed by the single crystal X-ray diffractometry. The key feature of the method is the simplicity of the diastereomeric separation.
Details
- ISSN :
- 15738353 and 00093122
- Volume :
- 56
- Database :
- OpenAIRE
- Journal :
- Chemistry of Heterocyclic Compounds
- Accession number :
- edsair.doi...........3ee1454e5c77689a8ee944227d41d69a