N-Heterocyclic Carbene-Catalyzed Atroposelective Synthesis of 5-Indo-1-yl Pyran-2-ones with an N−C axis from Enals

Linxue Zhang; Qianqian Wu; Min Ren; Hailong Zhang; Xiaoxiang Zhang; Jinhua Liu; Zhenqian Fu

doi:10.1002/adsc.202300686

N-Heterocyclic Carbene-Catalyzed Atroposelective Synthesis of 5-Indo-1-yl Pyran-2-ones with an N−C axis from Enals

Linxue Zhang, Qianqian Wu, Min Ren, Hailong Zhang, Xiaoxiang Zhang, Jinhua Liu, Zhenqian Fu

SCHOOL OF FLEXIBLE ELECTRONICS(FUTURE TECHNOLOGIES)|INSTITUTE OF ADVANCED MATERIALS(IAM)

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

9 Scopus citations

Abstract

A variety of 5-indo-1-yl pyran-2-ones with an N−C axis were prepared via a carbene-catalyzed oxidative [3+3] annulation of indole-1-pyruvate esters and enals. Asymmetric construction of pyran-2-one ring from enals ensures the realization of this strategy. The resulting compounds were converted into axially chiral N-arylindoles with an N−C axis via a cycloaddtion aromatization.

Original language	English
Pages (from-to)	3467-3472
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	365
Issue number	20
DOIs	https://doi.org/10.1002/adsc.202300686
State	Published - 24 Oct 2023

Keywords

Asymmetric catalysis
C−N axis
N-arylindoles
N-heterocyclic carbene
α,β-unsaturated aldehyde

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10.1002/adsc.202300686

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title = "N-Heterocyclic Carbene-Catalyzed Atroposelective Synthesis of 5-Indo-1-yl Pyran-2-ones with an N−C axis from Enals",

abstract = "A variety of 5-indo-1-yl pyran-2-ones with an N−C axis were prepared via a carbene-catalyzed oxidative [3+3] annulation of indole-1-pyruvate esters and enals. Asymmetric construction of pyran-2-one ring from enals ensures the realization of this strategy. The resulting compounds were converted into axially chiral N-arylindoles with an N−C axis via a cycloaddtion aromatization.",

keywords = "Asymmetric catalysis, C−N axis, N-arylindoles, N-heterocyclic carbene, α,β-unsaturated aldehyde",

author = "Linxue Zhang and Qianqian Wu and Min Ren and Hailong Zhang and Xiaoxiang Zhang and Jinhua Liu and Zhenqian Fu",

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T1 - N-Heterocyclic Carbene-Catalyzed Atroposelective Synthesis of 5-Indo-1-yl Pyran-2-ones with an N−C axis from Enals

AU - Zhang, Linxue

AU - Wu, Qianqian

AU - Ren, Min

AU - Zhang, Hailong

AU - Zhang, Xiaoxiang

AU - Liu, Jinhua

AU - Fu, Zhenqian

PY - 2023/10/24

Y1 - 2023/10/24

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AB - A variety of 5-indo-1-yl pyran-2-ones with an N−C axis were prepared via a carbene-catalyzed oxidative [3+3] annulation of indole-1-pyruvate esters and enals. Asymmetric construction of pyran-2-one ring from enals ensures the realization of this strategy. The resulting compounds were converted into axially chiral N-arylindoles with an N−C axis via a cycloaddtion aromatization.

KW - Asymmetric catalysis

KW - C−N axis

KW - N-arylindoles

KW - N-heterocyclic carbene

KW - α,β-unsaturated aldehyde

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DO - 10.1002/adsc.202300686

M3 - 文章

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SN - 1615-4150

VL - 365

SP - 3467

EP - 3472

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 20

ER -

N-Heterocyclic Carbene-Catalyzed Atroposelective Synthesis of 5-Indo-1-yl Pyran-2-ones with an N−C axis from Enals

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Keywords

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