Phosphine-catalyzed enantioselective [4 + 1] annulation of oxindoles with allenic ketones for the construction of spirocyclopentene oxindoles
Literature Information
Publication Date
2021-06-10
DOI
10.1039/D1QO00669J
Impact Factor
5.281
Authors
Huanzhen Ni
View Original
Abstract
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.
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Organic Chemistry Frontiers
CiteScore:
7.8
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8.7%
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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
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Molecular Formula:
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