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",

pages = "2136--2146",

journal = "Journal of the Chinese Chemical Society",

issn = "0009-4536",

publisher = "John Wiley and Sons Inc.",

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}

TY - JOUR

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

UR - https://www.scopus.com/pages/publications/85170705268

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DO - 10.1002/jccs.202300328

M3 - Article

AN - SCOPUS:85170705268

SN - 0009-4536

VL - 70

SP - 2136

EP - 2146

JO - Journal of the Chinese Chemical Society

JF - Journal of the Chinese Chemical Society

IS - 12

ER -

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

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