Efficient Access to 2-Pyrones via Carbene-Catalyzed Oxidative [3+3] Reactions between Enals and Nitrogen Ylides

Pengcheng Zheng; Chengcheng Li; Chengli Mou; Dingwu Pan; Shuquan Wu; Wei Xue; Zhichao Jin; Yonggui Robin Chi

doi:10.1002/ajoc.201900153

Efficient Access to 2-Pyrones via Carbene-Catalyzed Oxidative [3+3] Reactions between Enals and Nitrogen Ylides

Pengcheng Zheng, Chengcheng Li, Chengli Mou, Dingwu Pan, Shuquan Wu, Wei Xue^*, Zhichao Jin, Yonggui Robin Chi

^*Corresponding author for this work

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

19 Citations (Scopus)

Abstract

Pyrones are important structural units in natural products and synthetic functional molecules. Here, we report a carbene-catalyzed oxidative [3+3] cycloaddition reaction between enals and nitrogen ylides for quick access to 2-pyrones. Inexpensive and easily prepared 2′-pyridinium acetophenone bromide salts are used as precursors of pyridinium ylides to react with enals in our catalytic reactions.

Original language	English
Pages (from-to)	1067-1070
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	8
Issue number	7
DOIs	https://doi.org/10.1002/ajoc.201900153
Publication status	Published - Jul 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Organic Chemistry

Keywords

cycloaddition
enals
NHC catalysis
organocatalysis
ylides

Access to Document

10.1002/ajoc.201900153

Cite this

@article{d431050430f84f62afbd0e1ec6225c36,

title = "Efficient Access to 2-Pyrones via Carbene-Catalyzed Oxidative [3+3] Reactions between Enals and Nitrogen Ylides",

abstract = "Pyrones are important structural units in natural products and synthetic functional molecules. Here, we report a carbene-catalyzed oxidative [3+3] cycloaddition reaction between enals and nitrogen ylides for quick access to 2-pyrones. Inexpensive and easily prepared 2′-pyridinium acetophenone bromide salts are used as precursors of pyridinium ylides to react with enals in our catalytic reactions.",

keywords = "cycloaddition, enals, NHC catalysis, organocatalysis, ylides",

author = "Pengcheng Zheng and Chengcheng Li and Chengli Mou and Dingwu Pan and Shuquan Wu and Wei Xue and Zhichao Jin and Chi, {Yonggui Robin}",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

month = jul,

doi = "10.1002/ajoc.201900153",

language = "English",

volume = "8",

pages = "1067--1070",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

number = "7",

}

TY - JOUR

T1 - Efficient Access to 2-Pyrones via Carbene-Catalyzed Oxidative [3+3] Reactions between Enals and Nitrogen Ylides

AU - Zheng, Pengcheng

AU - Li, Chengcheng

AU - Mou, Chengli

AU - Pan, Dingwu

AU - Wu, Shuquan

AU - Xue, Wei

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2019/7

Y1 - 2019/7

N2 - Pyrones are important structural units in natural products and synthetic functional molecules. Here, we report a carbene-catalyzed oxidative [3+3] cycloaddition reaction between enals and nitrogen ylides for quick access to 2-pyrones. Inexpensive and easily prepared 2′-pyridinium acetophenone bromide salts are used as precursors of pyridinium ylides to react with enals in our catalytic reactions.

AB - Pyrones are important structural units in natural products and synthetic functional molecules. Here, we report a carbene-catalyzed oxidative [3+3] cycloaddition reaction between enals and nitrogen ylides for quick access to 2-pyrones. Inexpensive and easily prepared 2′-pyridinium acetophenone bromide salts are used as precursors of pyridinium ylides to react with enals in our catalytic reactions.

KW - cycloaddition

KW - enals

KW - NHC catalysis

KW - organocatalysis

KW - ylides

UR - http://www.scopus.com/inward/record.url?scp=85065666042&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85065666042&partnerID=8YFLogxK

U2 - 10.1002/ajoc.201900153

DO - 10.1002/ajoc.201900153

M3 - Article

AN - SCOPUS:85065666042

SN - 2193-5807

VL - 8

SP - 1067

EP - 1070

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 7

ER -

Efficient Access to 2-Pyrones via Carbene-Catalyzed Oxidative [3+3] Reactions between Enals and Nitrogen Ylides

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

Other files and links

Fingerprint

Cite this