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

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...

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Bibliographic Details
Published in:Journal of the Chinese Chemical Society (Taipei) 2023-12, Vol.70 (12), p.2136-2146
Main Authors: Wu, Pei‐Shan, Liou, Yan‐Cheng, Marri, Gangababu, Chen, Yi‐Ru, Wu, Jia‐Rong, Lin, Wenwei
Format: Article
Language:English
Subjects:
azomethine ylides
cycloaddition
vinyl para‐quinone methide
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Summary: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). 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.
ISSN:0009-4536
2192-6549
DOI:10.1002/jccs.202300328