Enantiopure Chiral Derivatives of the Fragrance Materials Majantol and Sila-majantol: A Bioisosteric Carbon/Silicon Switch with Drastic Effects on the Sensory Characteristics

详细信息    查看全文

• 作者：Thomas Schmid ; Jü ; rgen O. Daiss ; Rainer Ilg ; Horst Surburg ; and Reinhold Tacke
• 刊名：Organometallics
• 出版年：2003
• 出版时间：October 13, 2003
• 年：2003
• 卷：22
• 期：21
• 页码：4343 - 4346
• 全文大小：68K
• 年卷期：v.22,no.21(October 13, 2003)
• ISSN：1520-6041

文摘

The C/Si analogues 2-methyl-2-(3-methylbenzyl)but-3-en-1-ol (2a) and (hydroxymethyl)methyl(3-methylbenzyl)vinylsilane (2b) are chiral derivatives ofthe achiral fragrance materials majantol (1a) and sila-majantol (1b). Compounds 2a and 2b were synthesizedas racemates, and the respective (+)- and (-)-enantiomers were obtained by chromatographic resolution(HPLC) of rac-2a and rac-2b using a chiral stationaryphase. The enantiomerically pure compounds (+)-2a,(-)-2a, (+)-2b, and (-)-2b (optical rotations determinedin methanol) were studied for their sensory properties.Both the odor character and the odor intensity of thesilicon compounds (+)-2b and (-)-2b differ totallyfrom those of the respective carbon analogues (+)-2a and(-)-2a.