4.3 Article

Synthesis of chromeno[4,3-b]pyrrolidines from azomethine ylides and vinyl para-quinone methides via (3?+?2) cycloaddition/oxa-1,6-addition

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Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/jccs.202300328

Keywords

azomethine ylides; cycloaddition; vinyl para-quinone methide

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An efficient synthesis of chromeno[4,3-b]pyrrolidines has been developed via a mild base-catalyzed reaction, achieving excellent diastereoselectivity.
An efficient synthesis of chromeno[4,3-b]pyrrolidines has been successfully developed. This strategy involves a base-catalyzed reaction of p-VQMs and o-hydroxy azomethine ylides via (3 + 2) cycloaddition/oxa-1,6-addition reaction sequence. The reaction condition is mild, and a series of chromeno[4,3-b]pyrrolidines were obtained in 49-95% yields with excellent diastereoselectivity (dr > 20:1).

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