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

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

Xuefeng Liang,‡^a Weijian Ye,‡^a Waygen Thor,

‡^b Lantian Sun,^b Bo Wang,^b Shuzhong He,

*^c Yuen-Kit Cheng*^b and Chi-Sing Lee

*^ab

Author affiliations

* Corresponding authors

^a Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Lishui Road, Shenzhen 518055, China

^b Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR
E-mail: cslee-chem@hkbu.edu.hk

^c School of Pharmaceutical Sciences, Guizhou University, Guiyang, Guizhou 550025, China

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.

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Article information

DOI: https://doi.org/10.1039/D0QO00049C
Article type: Research Article
Submitted: 10 Jan 2020
Accepted: 14 Feb 2020
First published: 19 Feb 2020

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Org. Chem. Front., 2020,7, 840-845

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

X. Liang, W. Ye, W. Thor, L. Sun, B. Wang, S. He, Y. Cheng and C. Lee, Org. Chem. Front., 2020, 7, 840 DOI: 10.1039/D0QO00049C

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Organic Chemistry Frontiers

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

Abstract

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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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