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

Pei Shan Wu; Yan Cheng Liou; Gangababu Marri; Yi Ru Chen; Jia Rong Wu; Wenwei Lin

doi:10.1002/jccs.202300328

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

Pei Shan Wu, Yan Cheng Liou, Gangababu Marri, Yi Ru Chen, Jia Rong Wu, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

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).

Original language	English
Pages (from-to)	2136-2146
Number of pages	11
Journal	Journal of the Chinese Chemical Society
Volume	70
Issue number	12
DOIs	https://doi.org/10.1002/jccs.202300328
Publication status	Published - 2023 Dec

Keywords

azomethine ylides
cycloaddition
vinyl para-quinone methide

ASJC Scopus subject areas

General Chemistry

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10.1002/jccs.202300328

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

abstract = "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).",

keywords = "azomethine ylides, cycloaddition, vinyl para-quinone methide",

author = "Wu, {Pei Shan} and Liou, {Yan Cheng} and Gangababu Marri and Chen, {Yi Ru} and Wu, {Jia Rong} and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} 2023 The Chemical Society Located in Taipei & Wiley-VCH GmbH.",

year = "2023",

month = dec,

doi = "10.1002/jccs.202300328",

language = "English",

volume = "70",

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journal = "Journal of the Chinese Chemical Society",

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T1 - Synthesis of chromeno[4,3-b]pyrrolidines from azomethine ylides and vinyl para-quinone methides via (3 + 2) cycloaddition/oxa-1,6-addition

AU - Wu, Pei Shan

AU - Liou, Yan Cheng

AU - Marri, Gangababu

AU - Chen, Yi Ru

AU - Wu, Jia Rong

AU - Lin, Wenwei

PY - 2023/12

Y1 - 2023/12

N2 - 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).

AB - 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).

KW - azomethine ylides

KW - cycloaddition

KW - vinyl para-quinone methide

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

Abstract

Keywords

ASJC Scopus subject areas

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