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Figure S2. Representative chiral-HPLC analysis of rac-5b and (S) 5b. The enantiomeric ratio was determined by HPLC analysis in comparison with racemic material (CHIRAL PAK IB column, 95.0/5.0 isocratic n-heptane/2-propanol, 0.5 mL/min, major isomer: tR = 23.02 min, UV detection at 254.0 nm, 25 ºC). a Reactions conditions: toluene (1.5 M), 1.0 equiv of the ketone, 1.2 equiv of PNA and 1.4 equiv of the amino ester at 60 °C 24h. 4. Synthesis Procedures of 5a-p
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A practical and strightforward approach that enables for the first time, the synthesis of enantiomerically pure 1,4,5-
trisubstituted, 1,5-disubstituted, and fused 1,2,3 triazoles derivatives has been developed. The synthesis employs
enantiomerically pure amino esters derived from amino acids and commercially available ketones under metla-free
cond...
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Context 1
... products were obtained with 71% and 63% yield respectively. Finally, the free carboxylic acid derivative was prepared by hydrolysis of 5a in acidic conditions. Fortunately, the carboxylic acid derivative 9a (Fig. S39. ESI) was obtained with a 90% yield, besides no racemization was detected by 1 H-NMR spectra of the crude reaction mixture (see Fig. S40 ESI). Notably, attempts to prepare unprotected derivative 9a directly from cholestanone 3 and phenylalanine failed due to the insolubility of the amino acid in ...Context 2
... Information S37 Figure S14. 1 H-NMR (400 MHz, CDCl 3 ) and 13 C NMR (100 MHz, CDCl 3 ) Spectra of 5i. ...Similar publications
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