Construction of cyclopenta[: B] pyran-2-ones via chemoselective (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes

Xuefeng Liang; Weijian Ye; Waygen Thor; Lantian Sun; Bo Wang; Shuzhong He; Yuen Kit CHENG; Chi Sing LEE

doi:10.1039/d0qo00049c

Construction of cyclopenta[: B] pyran-2-ones via chemoselective (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes

Xuefeng Liang, Weijian Ye, Waygen Thor, Lantian Sun, Bo Wang, Shuzhong He^*, Yuen Kit CHENG^*, Chi Sing LEE^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

8 Citations (Scopus)

Abstract

A method for synthesising cyclopenta[b]pyran-2-ones through direct (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes is described. In the presence of Pd₂(dba)₃/dppe in toluene, a series of 2-pyrones undergo chemoselective (3 + 2) cycloaddition with vinyl cyclopropanes and afford cyclopenta[b]pyran-2-ones in high yields (78-96%). The trans/cis ratio of the cycloadducts has been optimised up to 10:1. The proposed mechanism of this cycloaddition has been rationalised by computational studies.

Original language	English
Pages (from-to)	840-845
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	7
Issue number	6
DOIs	https://doi.org/10.1039/d0qo00049c
Publication status	Published - 21 Mar 2020

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Organic Chemistry

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@article{ccfb068147f34616949d7f9ebe155c5e,

title = "Construction of cyclopenta[: B] pyran-2-ones via chemoselective (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes",

abstract = "A method for synthesising cyclopenta[b]pyran-2-ones through direct (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes is described. In the presence of Pd2(dba)3/dppe in toluene, a series of 2-pyrones undergo chemoselective (3 + 2) cycloaddition with vinyl cyclopropanes and afford cyclopenta[b]pyran-2-ones in high yields (78-96%). The trans/cis ratio of the cycloadducts has been optimised up to 10:1. The proposed mechanism of this cycloaddition has been rationalised by computational studies.",

author = "Xuefeng Liang and Weijian Ye and Waygen Thor and Lantian Sun and Bo Wang and Shuzhong He and CHENG, {Yuen Kit} and LEE, {Chi Sing}",

note = "Funding Information: We gratefully acknowledge the National Natural Science Foundation of China (Grants 21562011 and 21871017), Peking University Shenzhen Graduate School and Hong Kong Baptist University (RC-SGT2/18-19/SCI/005 and RC-ICRS-18-19-01A) for the financial support of this work.",

year = "2020",

month = mar,

day = "21",

doi = "10.1039/d0qo00049c",

language = "English",

volume = "7",

pages = "840--845",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

number = "6",

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TY - JOUR

T1 - Construction of cyclopenta[

T2 - B] pyran-2-ones via chemoselective (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes

AU - Liang, Xuefeng

AU - Ye, Weijian

AU - Thor, Waygen

AU - Sun, Lantian

AU - Wang, Bo

AU - He, Shuzhong

AU - CHENG, Yuen Kit

AU - LEE, Chi Sing

N1 - Funding Information: We gratefully acknowledge the National Natural Science Foundation of China (Grants 21562011 and 21871017), Peking University Shenzhen Graduate School and Hong Kong Baptist University (RC-SGT2/18-19/SCI/005 and RC-ICRS-18-19-01A) for the financial support of this work.

PY - 2020/3/21

Y1 - 2020/3/21

N2 - A method for synthesising cyclopenta[b]pyran-2-ones through direct (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes is described. In the presence of Pd2(dba)3/dppe in toluene, a series of 2-pyrones undergo chemoselective (3 + 2) cycloaddition with vinyl cyclopropanes and afford cyclopenta[b]pyran-2-ones in high yields (78-96%). The trans/cis ratio of the cycloadducts has been optimised up to 10:1. The proposed mechanism of this cycloaddition has been rationalised by computational studies.

AB - A method for synthesising cyclopenta[b]pyran-2-ones through direct (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes is described. In the presence of Pd2(dba)3/dppe in toluene, a series of 2-pyrones undergo chemoselective (3 + 2) cycloaddition with vinyl cyclopropanes and afford cyclopenta[b]pyran-2-ones in high yields (78-96%). The trans/cis ratio of the cycloadducts has been optimised up to 10:1. The proposed mechanism of this cycloaddition has been rationalised by computational studies.

UR - http://www.scopus.com/inward/record.url?scp=85082122771&partnerID=8YFLogxK

U2 - 10.1039/d0qo00049c

DO - 10.1039/d0qo00049c

M3 - Journal article

AN - SCOPUS:85082122771

SN - 2052-4110

VL - 7

SP - 840

EP - 845

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 6

ER -

Construction of cyclopenta[: B] pyran-2-ones via chemoselective (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes

Abstract

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