SYNTHESIS, RESOLUTION AND ABSOLUTE-CONFIGURATION DETERMINATION OF (S)-4-FORMYL-5-HYDROXY[2.2]PARACYCLOPHANE AND (R)-4-FORMYL-5-HYDROXY[2.2]PARACYCLOPHANE AND ITS APPLICATION IN THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS

Authors
ANTONOV DY BELOKON YN IKONNIKOV NS ORLOVA SA PISAREVSKY AP RAEVSKI NI ROZENBERG VI SERGEEVA EV STRUCHKOV YT TARAROV VI VORONTSOV EV
Citation
Dy. Antonov et al., SYNTHESIS, RESOLUTION AND ABSOLUTE-CONFIGURATION DETERMINATION OF (S)-4-FORMYL-5-HYDROXY[2.2]PARACYCLOPHANE AND (R)-4-FORMYL-5-HYDROXY[2.2]PARACYCLOPHANE AND ITS APPLICATION IN THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS, Journal of the Chemical Society. Perkin transactions. I, (14), 1995, pp. 1873-1879
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
14
Year of publication
1995
Pages
1873 - 1879
Database
ISI
SICI code
0300-922X(1995):14<1873:SRAADO>2.0.ZU;2-M
Abstract
Racemic (R, S)-4-formyl-5-hydroxy[2.2]paracyclophane (FHPC) was resolv ed into enantiomers via its Schiff's base with (S)- and (R)-alpha-phen ylethylamine (alpha-PEAM) and its absolute configuration was determine d by an X-ray diffraction structural study. Scalemic FHPC or its deriv atives can be used as chiral auxiliaries for the asymmetric synthesis of beta-hydroxy-alpha-amino acids and alpha-methylphenylalanine with e es ranging mostly from 45 to 98%.