Synthesis, resolution and absolute configuration determination of (S)- and (R)-4-formyl-5-hydroxy [2.2]paracyclophane and its application in the asymmetric synthesis of α-amino acids
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 14,p. 1873-1879
- https://doi.org/10.1039/p19950001873
Abstract
Racemic (R,S)-4-formyl-5-hydroxy[2.2]paracyclophane (FHPC) was resolved into enantiomers via its Schiff's base with (S)- and (R)-α-phenylethylamine (α-PEAM) and its absolute configuration was determined by an X-ray diffraction structural study. Scalemic FHPC or its derivatives can be used as chiral auxiliaries for the asymmetric synthesis of β-hydroxy-α-amino acids and α-methylphenylalanine with ees ranging mostly from 45 to 98%.Keywords
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