Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids

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• 作者：Zhenyu Yang ; Ying He ; F. Dean Toste
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：August 10, 2016
• 年：2016
• 卷：138
• 期：31
• 页码：9775-9778
• 全文大小：390K
• 年卷期：0
• ISSN：1520-5126

文摘

Herein is reported the direct asymmetric addition of phenol nucleophiles to benzopyrylium salts as a means to produce enantioenriched flavonoid-like compounds. This enantioselective C–C bond construction was achieved through a chiral anion phase-transfer strategy that mimics the proposed biosynthesis of this structurally diverse set of natural products. The utility of this methodology was demonstrated in enantioselective synthesis of a 2,8-dioxabicyclo[3.3.1]nonane and a 2,4-diarylbenzopyran.