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

文献信息

发布日期 2019-12-09

DOI 10.1039/C9QO01349K

影响因子 5.281

作者

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

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摘要

(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.

期刊推荐

Chemical Communications

Saudi Pharmaceutical Journal

Russian Journal of Bioorganic Chemistry

Nature Medicine

New Journal of Chemistry

Journal of Saudi Chemical Society

Journal of Peptide Science

Current Opinion in Solid State & Materials Science

Russian Journal of Organic Chemistry

Russian Chemical Bulletin

来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 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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来源期刊

Organic Chemistry Frontiers

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