Citation: Li Yao, Chen Kunquan, Zhang Yan, Sun Dequn, Ye Song. N-Heterocyclic carbene-catalyzed[4 + 2] cyclization of α-chloroaldehydes and aurones: Highly enantioselective synthesis of benzofuran-fused dihydropyran-2-ones[J]. Chinese Chemical Letters, ;2018, 29(8): 1209-1211. doi: 10.1016/j.cclet.2018.03.003 shu

N-Heterocyclic carbene-catalyzed[4 + 2] cyclization of α-chloroaldehydes and aurones: Highly enantioselective synthesis of benzofuran-fused dihydropyran-2-ones

Li Yao ^a,b,1 ,
Chen Kunquan ^b,c,1 ,
Zhang Yan ^b ,
Sun Dequn ^a,, ,
Ye Song ^b,c,,

a.
Marine College, Shandong University at Weihai, Weihai 264209, China
b.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Sun Dequn, dequn.sun@sdu.edu.cn Ye Song, songye@iccas.ac.cn

Received Date: 3 January 2018
Revised Date: 3 February 2018
Accepted Date: 1 March 2018
Available Online: 3 August 2018

Figures(4)

The chiral N-heterocyclic carbene-catalyzed[4 + 2] annulation of α-chloroaldehydes and aurones was developed, giving the corresponding benzofuran-fused dihydropyranones in good to high yields with good diastereoselectivities and excellent enantioselectivities. The catalytic cycle features with the generation of enolate from chloroaldehdye and its following[4 + 2] cycloaddtion with aurones.
- Carbene catalysis,
- Annulation,
- Enantioselectivity,
- Benzofuran,
- Dihydropranone
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