(4 + 3) cycloadditions of allenyl ether-derived oxygen-stabilized oxyallyls with furans

文献情報

出版日 2019-12-09

DOI 10.1039/C9QO01349K

インパクトファクター 5.281

著者

Xian Huang, Waygen Thor, Xiangyu Feng, Liangliang Kang, Min Yang, Chi-Sing Lee, Yuen-Kit Cheng, Shuzhong He

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要旨

(4 + 3) cycloadditions between allenyl ethers and furans are described. The reaction features an in situ formation of oxygen-stabilized oxyallyls via epoxidations of allenyl ethers in the presence of H2PO4−. The multiple interactions between the oxygen-stabilized oxyallyl species and H2PO4− were studied using DFT calculations for rationalization of the regio- and diastereoselectivity of this cycloaddition. The utilities of this cycloaddition have been demonstrated by converting the (4 + 3) cycloadduct into the cyclohepta[b]benzofuran skeleton of frondosin B in two steps.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

(4 + 3) cycloadditions of allenyl ether-derived oxygen-stabilized oxyallyls with furans

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