Chiral Boron Complex-Promoted Asymmetric Diels–Alder Cycloaddition and Its Application in Natural Product Synthesis

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• 作者：Xia Li ; Jianguang Han ; Alexander X. Jones ; Xiaoguang Lei
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：January 15, 2016
• 年：2016
• 卷：81
• 期：2
• 页码：458-468
• 全文大小：800K
• ISSN：1520-6904

文摘

An efficient method for the asymmetric Diels–Alder cycloaddition of 2′-hydroxychalcones with acyclic or cyclic dienes has been successfully developed. The Diels–Alder cycloaddition is mediated by a chiral boron complex with VANOL, affording the corresponding products in high yields and with excellent diastereo- and enantioselectivities. This reaction enabled the enantioselective construction of cyclohexene skeletons crucial for the total synthesis of a number of Diels–Alder-type natural products (?)-nicolaioidesin C, (?)-panduratine A, (?)-kuwanon I, (+)-kuwanon J, and (?)-brosimones A and B.