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

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.

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-06, Vol.14 (22), p.5059-5064
Main Authors: Han, Xiaoyu, Ni, Huanzhen, Chan, Wai-Lun, Gai, Xikun, Wang, Yongjiang, Lu, Yixin
Format: Article
Language:English
Subjects:
Catalysis
Chemistry Techniques, Synthetic
Coumarins - chemistry
Ketones - chemistry
Phosphines - chemistry
Pyrans - chemical synthesis
Pyrans - chemistry
Stereoisomerism
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Description
Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob00955g