Lewis Acid-Catalyzed Formal [2π+2σ] Cycloaddition of Bicyclobutanes with Quinoxalin-2(1H)‑ones: Access to Quinoxaline-Fused Aza-Bicyclo[2.1.1]hexanes

Kuan Zhang; Shanghui Tian; Wenke Li; Xu Yang; Xin Hua Duan; Li Na Guo; Pengfei Li

doi:10.1021/acs.orglett.4c01775

Lewis Acid-Catalyzed Formal [2π+2σ] Cycloaddition of Bicyclobutanes with Quinoxalin-2(1H)‑ones: Access to Quinoxaline-Fused Aza-Bicyclo[2.1.1]hexanes

Kuan Zhang
, Shanghui Tian
, Wenke Li
, Xu Yang
, Xin Hua Duan
, Li Na Guo
, Pengfei Li

Xi'an Jiaotong University

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

23 Scopus citations

Abstract

An efficient synthesis of quinoxaline-fused aza-bicyclo[2.1.1]hexanes bearing multiple quaternary carbon centers via the intermolecular [2π+2σ] cycloaddition of bicyclo[1.1.0]butanes and quinoxalin-2(1H)-ones, facilitated by Lewis acid catalysis, is presented. This reaction is carried out under mild conditions and exhibits a broad substrate scope and excellent functional group tolerance.

Original language	English
Pages (from-to)	5482-5487
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	26
DOIs	https://doi.org/10.1021/acs.orglett.4c01775
State	Published - 5 Jul 2024

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10.1021/acs.orglett.4c01775

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title = "Lewis Acid-Catalyzed Formal [2π+2σ] Cycloaddition of Bicyclobutanes with Quinoxalin-2(1H)‑ones: Access to Quinoxaline-Fused Aza-Bicyclo[2.1.1]hexanes",

abstract = "An efficient synthesis of quinoxaline-fused aza-bicyclo[2.1.1]hexanes bearing multiple quaternary carbon centers via the intermolecular [2π+2σ] cycloaddition of bicyclo[1.1.0]butanes and quinoxalin-2(1H)-ones, facilitated by Lewis acid catalysis, is presented. This reaction is carried out under mild conditions and exhibits a broad substrate scope and excellent functional group tolerance.",

author = "Kuan Zhang and Shanghui Tian and Wenke Li and Xu Yang and Duan, \{Xin Hua\} and Guo, \{Li Na\} and Pengfei Li",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

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doi = "10.1021/acs.orglett.4c01775",

language = "英语",

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TY - JOUR

T1 - Lewis Acid-Catalyzed Formal [2π+2σ] Cycloaddition of Bicyclobutanes with Quinoxalin-2(1H)‑ones

T2 - Access to Quinoxaline-Fused Aza-Bicyclo[2.1.1]hexanes

AU - Zhang, Kuan

AU - Tian, Shanghui

AU - Li, Wenke

AU - Yang, Xu

AU - Duan, Xin Hua

AU - Guo, Li Na

AU - Li, Pengfei

PY - 2024/7/5

Y1 - 2024/7/5

N2 - An efficient synthesis of quinoxaline-fused aza-bicyclo[2.1.1]hexanes bearing multiple quaternary carbon centers via the intermolecular [2π+2σ] cycloaddition of bicyclo[1.1.0]butanes and quinoxalin-2(1H)-ones, facilitated by Lewis acid catalysis, is presented. This reaction is carried out under mild conditions and exhibits a broad substrate scope and excellent functional group tolerance.

AB - An efficient synthesis of quinoxaline-fused aza-bicyclo[2.1.1]hexanes bearing multiple quaternary carbon centers via the intermolecular [2π+2σ] cycloaddition of bicyclo[1.1.0]butanes and quinoxalin-2(1H)-ones, facilitated by Lewis acid catalysis, is presented. This reaction is carried out under mild conditions and exhibits a broad substrate scope and excellent functional group tolerance.

UR - https://www.scopus.com/pages/publications/85196938461

U2 - 10.1021/acs.orglett.4c01775

DO - 10.1021/acs.orglett.4c01775

M3 - 文章

C2 - 38913035

AN - SCOPUS:85196938461

SN - 1523-7060

VL - 26

SP - 5482

EP - 5487

JO - Organic Letters

JF - Organic Letters

IS - 26

ER -

Lewis Acid-Catalyzed Formal [2π+2σ] Cycloaddition of Bicyclobutanes with Quinoxalin-2(1H)‑ones: Access to Quinoxaline-Fused Aza-Bicyclo[2.1.1]hexanes

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