Abstract
Reduction of symmetrical bis-isoquinolinium derivatives with sodium borohydride generates normally a mixture of three 1,2,3,4-tetrahydroisoquinoline stereoisomers. In a series of 8-isopropyl analogues, chiral resolution failed for the analogues with propyl and m-xylyl linkers since two and one peaks respectively were detected by HPLC. Further analysis by MS and CD of both peaks of the propyl analogue revealed that each peak corresponds to an enantiomer. Conformational analysis and X-ray cristallography showed a folded conformation of the propyl and m-xylyl analogues responsible for the observed stereoselectivity following the reduction step. Additional 1H NMR investigations confirm structural features detected by theoretical analysis.
Original language | English |
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Pages (from-to) | 435-440 |
Number of pages | 6 |
Journal | Journal of molecular structure |
Volume | 1074 |
DOIs | |
Publication status | Published - 25 Sept 2014 |
Keywords
- Borohydride
- Chiral HPLC
- Conformational analysis
- Selectivity
- Sterical hindrance
- X-ray crystallography
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Dive into the research topics of 'Structural analysis of some bis-(8-isopropyl-isoquinolinium) derivatives reveals a preferential folded conformation leading to a stereoselective attack by sodium borohydride'. Together they form a unique fingerprint.Equipment
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Physical Chemistry and characterization(PC2)
Johan Wouters (Manager) & Carmela Aprile (Manager)
Technological Platform Physical Chemistry and characterizationFacility/equipment: Technological Platform