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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 1
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Original Articles

Pictet-Spengler Cyclization of 3,3-Diphenylalanine (DIP) (III), Synthesis of Optically Pure 1,2,3,4-Tetrahydro-4-phenyl-3-isoquinolinecarboxylic Acids, Novel α-Amino Acids for Peptides of Biological Interest

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Pages 49-56 | Received 16 May 1994, Published online: 23 Sep 2006

References

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  • Analytical HPLC was performed with a Perkin Elmer Series 410 quaternary pump and LC-95 detector system, and a 4.6 × 100mm spherisorb silica 3 nm column (Sigma-Aldrich), hexane:EtOAc/95 : 5, flow rate = 1.0 mL/min, to give the peak of cis isomers 4a″, 4b″ at tR = 2.66 min, and trans isomers 4a′, 4b′ at tR = 3.30 min.
  • The stereo structures of trans and cis isomers were determermined by the coupling constants (1H NMR) of Ha and Hb. The experimental data showed that JHa-Hb = 10.1 Hz for the trans isomers 5a′, 5b′, and JHa-Hb = 5.1 Hz for the cis isomers 5a″, 5b″.

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