Phosphine-catalyzed activation of cyclopropenones: a versatile C3 synthon for (3+2) annulations with unsaturated electrophiles

He, Xin, Ma, Pengchen, Tang, Yuhai , Li, Jing, Shen, Shenyu, Lear, Martin, Houk, K.N. and Xu, Silong (2022) Phosphine-catalyzed activation of cyclopropenones: a versatile C3 synthon for (3+2) annulations with unsaturated electrophiles. Chemical Science, 13 (43). ISSN 2041-6539

Full content URL: https://doi.org/10.1039/d2sc04092a

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Phosphine-Catalyzed Activation of Cyclopropenones: A Versatile C3 Synthon for (3+2) Annulations with Unsaturated Electrophiles
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Abstract

We herein report a phosphine-catalyzed (3 + 2) annulation of cyclopropenones with a wide variety of electrophilic π systems, including aldehydes, ketoesters, imines, isocyanates, and carbodiimides, offering products of butenolides, butyrolactams, maleimides, and iminomaleimides, respectively, in high yields with broad substrate scope. An α-ketenyl phosphorous ylide is validated as the key intermediate, which undergoes preferential catalytic cyclization with aldehydes rather than stoichiometric Wittig olefinations. This phosphine-catalyzed activation of cyclopropenones thus supplies a versatile C3 synthon for formal cycloadditon reactions.

Keywords:organic chemistry, Organic methods
Subjects:F Physical Sciences > F160 Organic Chemistry
Divisions:College of Science > School of Chemistry
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ID Code:52200
Deposited On:22 Nov 2022 14:52

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