Iron-catalyzed boration of cinnamyl carbonates: a highly stereoselective approach to cyclopropylboronates

文献信息

发布日期 2019-02-20

DOI 10.1039/C8QO01163J

影响因子 5.281

作者

Yang Liu, Yuhan Zhou, Dong Li, Han Chen, Jinfeng Zhao, Jingping Qu

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摘要

An efficient approach to cyclopropylboronates via iron-catalyzed boration/cyclopropylation of cinnamyl carbonates is developed. The reactions of cinnamyl carbonates and B2pin2 (bis(pinacolato)diboron) proceed smoothly in tetrahydrofuran, catalyzed by ferric chloride/DPPP (1,3-bis(diphenlphosphino)propane). Thus, a wide range of cyclopropylboronates with broad functional-group compatibility was obtained in moderate to high yields (50%–95%) with excellent stereoselectivities (97 : 3–99 : 1 dr). This reaction represents the first iron-catalyzed boration of cinnamyl esters to synthesize cyclopropylboronates.

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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

Iron-catalyzed boration of cinnamyl carbonates: a highly stereoselective approach to cyclopropylboronates

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