A new approach to the synthesis of the single stereomers of the fragrances Phenoxanol, Citralis and Citralis Nitrile is reported. The key step of the synthesis is the asymmetric hydrogenation of (Z)- or (E)-3-methyl-5-phenyl-pent-2-en-1-ol, which leads to the single enantiomers of Phenoxanol from which both enantiomers of Citralis are obtained by oxidation. Treatment of these compounds with hydroxylamine finally led to Citralis Nitrile without any loss of enantiopurity. The odour profiles of the single enantiomers of these fragrances are reported as well.

Asymmetric catalysis in fragrance chemistry: a new synthetic approach to enantiopure Phenoxanol®, Citralis® and Citralis Nitrile®

MATTEOLI, Ugo;BERTOLDINI, Matteo;SCRIVANTI, Alberto
2007-01-01

Abstract

A new approach to the synthesis of the single stereomers of the fragrances Phenoxanol, Citralis and Citralis Nitrile is reported. The key step of the synthesis is the asymmetric hydrogenation of (Z)- or (E)-3-methyl-5-phenyl-pent-2-en-1-ol, which leads to the single enantiomers of Phenoxanol from which both enantiomers of Citralis are obtained by oxidation. Treatment of these compounds with hydroxylamine finally led to Citralis Nitrile without any loss of enantiopurity. The odour profiles of the single enantiomers of these fragrances are reported as well.
File in questo prodotto:
File Dimensione Formato  
SCRIVANTI_TETRAH_ASYMM_2007.pdf

non disponibili

Tipologia: Altro materiale relativo al prodotto (file audio, video, ecc.)
Licenza: Accesso chiuso-personale
Dimensione 181.11 kB
Formato Adobe PDF
181.11 kB Adobe PDF   Visualizza/Apri

I documenti in ARCA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10278/22732
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 22
  • ???jsp.display-item.citation.isi??? 22
social impact