Enantioselective Synthesis of 4H-Pyrans Through Organocatalytic Asymmetric Formal [3+3] Cycloadditions of 2-(1-Alkynyl)-2-alken-1-ones with β-Keto Esters

4H‐Pyran units are frequently present in molecules with significant biological and pharmaceutical activities. Herein, we present the first enantioselective formal [3+3] cycloaddition between 2‐(1‐alkynyl)‐2‐alken‐1‐ones and β‐keto esters catalyzed by a cyclohexyldiamine‐based thiourea‐tertiary amine...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2016-10, Vol.358 (19), p.3015-3020
Main Authors: Yue, Zhenting, Li, Wenbo, Liu, Lu, Wang, Cuihong, Zhang, Junliang
Format: Article
Language:English
Subjects:
4H-pyrans
[3+3] cycloaddition
bifunctional catalysts
eco-friendly reactions
enantioselectivities
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Summary:4H‐Pyran units are frequently present in molecules with significant biological and pharmaceutical activities. Herein, we present the first enantioselective formal [3+3] cycloaddition between 2‐(1‐alkynyl)‐2‐alken‐1‐ones and β‐keto esters catalyzed by a cyclohexyldiamine‐based thiourea‐tertiary amine bifunctional catalyst. Under the mild and eco‐friendly conditions, a wide range of polysubstituted 4H‐pyrans were obtained in moderate yields with good enantioselectivities.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600591