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Asymmetric Fluorinative Dearomatization of tryptophol Derivatives by Chiral Anion Phase-Transfer Catalysis

Chinese Journal of Chemistry 2018年第10期36卷 925-928页

作者： Xiao-Wei Liang Yue Cai Shu-LiYou State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 China School of Pharmacy East China University of Science and Technology 130Mei-Long Road Shanghai 200237 China

An asymmetric fluorinative dearomatization reaction of tryptophol derivatives was developed via chiral anion phase-transfer catalysis. Vari- ous fluorinated furoindolines were obtained in moderate to excellent yields and enantioselectivity in the presence of Selectfluor. The preliminary mecha- nistic studies suggested the existence of an in situ formed tryptophol boronic ester plays a critical role in determining the enantioselectivity. This method features the facile introduction of a fluorine atom in a highly enantioselective manner and construction of two contiguous quaternary stereogenic cen- ters.

关键词： asymmetric catalysis dearomatization fluorination organocatalysis phase-transfer catalysis tryptophol

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Enhancing the Yields of Phenolic Compounds during Fermentation Using <i>Saccharomyces cerevisiae</i>Strain 96581

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Food and Nutrition Sciences 2014年第21期5卷 2063-2070页

作者： Adam A. Banach Beng Guat Ooi Department of Chemistry Middle Tennessee State University Murfreesboro TN USA

Phenylethanol, tyrosol, and tryptophol are phenolic compounds or fusel alcohols formed via the Ehrlich pathway by yeast metabolism. These compounds can yield health benefits as well as contribute to the flavors and aromas of fermented food and beverages. This research shows that Saccharomyces cerevisiae Strain 96581 is capable of producing significantly higher levels of these three compounds when the precursor amino acids were supplemented into either the Chardonnay concentrate for wine-making or the malt concentrate for brewing English Ale. Strain 96581 can produce phenylethanol, tyrosol, and tryptophol as high as 434 mg/kg, 365 mg/kg, and 129 mg/kg, respectively, in the beer fermentation. The performance of Ale yeast WLP002 from White Labs Inc. was also analyzed for comparison. Strain 96581 outperformed WLP002 in the control beer, the amino acids supplemented beer, and the kiwi-beer background. This shows that Strain 96581 is more effective than WLP002 in converting the malt and the kiwi fruit supplements via its endogenous enzymes.

关键词： Phenolic Antioxidants Tyrosol tryptophol Phenylethanol Fermentation Technology

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