Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates

Jiru Shao; Caiyun An; Sunewang R. Wang

doi:10.1055/a-1526-7839

Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates

Jiru Shao
, Caiyun An
, Sunewang R. Wang^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

13 Scopus citations

Abstract

A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C-C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.

Original language	English
Pages (from-to)	4030-4041
Number of pages	12
Journal	Synthesis (Germany)
Volume	53
Issue number	21
DOIs	https://doi.org/10.1055/a-1526-7839
State	Published - 8 Jul 2021

Keywords

2-pyrones
Bronsted acid
carbocycles
cyclopropanes
heterocycles
ring expansion
synthetic methods

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10.1055/a-1526-7839

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title = "Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates",

abstract = "A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C-C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.",

keywords = "2-pyrones, Bronsted acid, carbocycles, cyclopropanes, heterocycles, ring expansion, synthetic methods",

author = "Jiru Shao and Caiyun An and Wang, \{Sunewang R.\}",

year = "2021",

month = jul,

day = "8",

doi = "10.1055/a-1526-7839",

language = "英语",

volume = "53",

pages = "4030--4041",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

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T1 - Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates

AU - Shao, Jiru

AU - An, Caiyun

AU - Wang, Sunewang R.

PY - 2021/7/8

Y1 - 2021/7/8

N2 - A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C-C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.

AB - A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C-C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.

KW - 2-pyrones

KW - Bronsted acid

KW - carbocycles

KW - cyclopropanes

KW - heterocycles

KW - ring expansion

KW - synthetic methods

UR - https://www.scopus.com/pages/publications/85109879095

U2 - 10.1055/a-1526-7839

DO - 10.1055/a-1526-7839

M3 - 文章

AN - SCOPUS:85109879095

SN - 0039-7881

VL - 53

SP - 4030

EP - 4041

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 21

ER -

Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates

Abstract

Keywords

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