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 › Article › peer-review

4 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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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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Construction of cyclopenta[ : B] pyran-2-ones via chemoselective (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes. / Liang, Xuefeng; Ye, Weijian; Thor, Waygen; Sun, Lantian; Wang, Bo; He, Shuzhong; CHENG, Yuen Kit ; LEE, Chi Sing.

In: Organic Chemistry Frontiers, Vol. 7, No. 6, 21.03.2020, p. 840-845.

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

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.

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

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