Rational design and organocatalytic enantioselective [1 + 4]-annulations of MBH carbonates with modified enones

Xing Guo; Boming Shen; Chang Liu; Hongyue Zhao; Xuechen Li; Peiyuan Yu; Pengfei Li

doi:10.1039/D2QO01670B

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Rational design and organocatalytic enantioselective [1 + 4]-annulations of MBH carbonates with modified enones†

Xing Guo,‡^ab Boming Shen,‡^a Chang Liu,^a Hongyue Zhao,^a Xuechen Li,

*^b Peiyuan Yu

*^a and Pengfei Li

*^a

Author affiliations

* Corresponding authors

^a Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology (SUSTech), Shenzhen, Guangdong, China
E-mail: yupy@sustech.edu.cn, lipf@sustech.edu.cn, flyli1980@gmail.com

^b Department of Chemistry, State Key Lab of Synthetic Chemistry, The University of Hong Kong, Hong Kong, China
E-mail: xuechenl@hku.hk

Abstract

According to the frontier molecular orbital theory, two types of modified enones have been designed and successfully applied in the chiral phosphine-catalyzed stereoselective [1 + 4]-annulation of Morita–Baylis–Hillman (MBH) carbonates for the first time. The reaction proceeds smoothly under mild conditions and exhibits excellent functional group tolerance, furnishing a broad scope of enantioenriched 2,3-dihydrofurans with high efficiency. DFT calculations have been applied to provide guidance for the design of additional enones and understand the origin of stereoselectivity. Importantly, this protocol further explores the scope of enones and enriches the chemistry of [1 + 4]-annulations of MBH carbonates for preparation of optically active multifunctional 2,3-dihydrofurans.

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Article information

DOI: https://doi.org/10.1039/D2QO01670B
Article type: Research Article
Submitted: 21 Oct 2022
Accepted: 14 Nov 2022
First published: 16 Nov 2022

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Org. Chem. Front., 2023,10, 150-156

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Rational design and organocatalytic enantioselective [1 + 4]-annulations of MBH carbonates with modified enones

X. Guo, B. Shen, C. Liu, H. Zhao, X. Li, P. Yu and P. Li, Org. Chem. Front., 2023, 10, 150 DOI: 10.1039/D2QO01670B

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Rational design and organocatalytic enantioselective [1 + 4]-annulations of MBH carbonates with modified enones†

Abstract

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Rational design and organocatalytic enantioselective [1 + 4]-annulations of MBH carbonates with modified enones

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