Issue 22, 2016
From the journal:

Organic & Biomolecular Chemistry

Highly enantioselective synthesis of dihydrocoumarin-fused dihydropyrans via the phosphine-catalyzed [4 + 2] annulation of allenones with 3-aroylcoumarins†

Xiaoyu Han,*a   Huanzhen Ni,bc   Wai-Lun Chan,b   Xikun Gai,a   Yongjiang Wanga  and  Yixin Lu*bc  

* Corresponding authors

a Zhejiang Provincial Key Laboratory for Chemical & Biological Processing Technology of Farm Products, School of Biological and Chemical Engineering/School of Light Industry, Zhejiang University of Science and Technology, Hangzhou, China
E-mail: chemhanxy@zust.edu.cn

b Department of Chemistry, Life Science Institute, National University of Singapore (NUS), 3 Science Drive 3, Singapore
E-mail: chmlys@nus.edu.sg

c Graduate School for Integrative Sciences & Engineering (NGS), Centre for Life Sciences (CeLS), National University of Singapore, #05-01, 28 Medical Drive, 117456 Singapore

Abstract

Phosphine-catalyzed [4 + 2] annulation between 3-aroylcoumarins and allenones has been developed. In the presence of a dipeptide phosphine catalyst 7, dihydrocoumarin-fused dihydropyrans were prepared in high yields and with excellent enantioselectivities.

Graphical abstract: Highly enantioselective synthesis of dihydrocoumarin-fused dihydropyrans via the phosphine-catalyzed [4 + 2] annulation of allenones with 3-aroylcoumarins

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Article information

DOI
https://doi.org/10.1039/C6OB00955G
Article type
Paper
Submitted
02 May 2016
Accepted
06 May 2016
First published
06 May 2016

Org. Biomol. Chem., 2016,14, 5059-5064

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Highly enantioselective synthesis of dihydrocoumarin-fused dihydropyrans via the phosphine-catalyzed [4 + 2] annulation of allenones with 3-aroylcoumarins

X. Han, H. Ni, W. Chan, X. Gai, Y. Wang and Y. Lu, Org. Biomol. Chem., 2016, 14, 5059 DOI: 10.1039/C6OB00955G

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