Phosphine-catalyzed enantioselective [4 + 1] annulation of oxindoles with allenic ketones for the construction of spirocyclopentene oxindoles

文献情報

出版日 2021-06-10

DOI 10.1039/D1QO00669J

インパクトファクター 5.281

著者

Huanzhen Ni

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要旨

A phosphine-catalyzed enantioselective [4 + 1] annulation between allenic ketones and oxindoles has been developed. This annulation reaction makes use of allenic ketones as dielectrophilic C4 synthons and oxindoles as nucleophilic C1 reaction partners. A range of 3-spirocyclopentene-2-oxindoles with quaternary stereogenic centers were prepared in high yields and with excellent enantioselectivities. Synthetic elaborations of the [4 + 1] annulation product led to a facile total synthesis of (+)-debromoflustramine B.

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

Phosphine-catalyzed enantioselective [4 + 1] annulation of oxindoles with allenic ketones for the construction of spirocyclopentene oxindoles

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