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

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• 作者：Ugo Matteoli ; Aless ; ra Ciappa ; Sara Bovo ; Matheo Bertoldini ; Alberto Scrivanti
• 刊名：Tetrahedron: Asymmetry
• 出版年：2007
• 出版时间：16 April 2007
• 年：2007
• 卷：18
• 期：6
• 页码：797-802
• 全文大小：181 K

文摘

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.