Carbonyl‐Oxygen‐Assisted KOMe‐Mediated Formal Hydration of 4‐Alkynones: Complete Regioselectivity in the One‐Pot Synthesis of 1,4‐Diketones under Mild Conditions

An effective carbonyl‐oxygen‐assisted transition‐metal‐free approach was developed for the one‐pot synthesis of 1,4‐diketones through the formal hydration of 4‐alkynones with complete regioselectivity under mild conditions. The reaction tolerates a wide range of functional groups, and the correspond...

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Bibliographic Details
Published in:European journal of organic chemistry 2018-04, Vol.2018 (13), p.1581-1588
Main Authors: Bai, Xue‐Ting, Zhang, Qian‐Qian, Zhang, Shuai, Chen, Dan‐Yun, Fu, Ji‐Ya, Zhu, Jun‐Yan, Wang, Yan‐Bo, Tang, Yan‐Ting
Format: Article
Language:English
Subjects:
Alkynes
Carbonyls
Cyclization
Diketones
Functional groups
Hydration
Ketones
Regioselectivity
Ring opening
Synthesis
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Summary:An effective carbonyl‐oxygen‐assisted transition‐metal‐free approach was developed for the one‐pot synthesis of 1,4‐diketones through the formal hydration of 4‐alkynones with complete regioselectivity under mild conditions. The reaction tolerates a wide range of functional groups, and the corresponding functionalized 1,4‐diketones were obtained in moderate to excellent yields (up to 94 %). Importantly, the complete regioselectivity was attributed to the fact that 2,3‐dihydrofuran intermediates were obtained as single products through the 5‐exo‐dig cyclization of 4‐alkynones; this was supported by control and isotope‐labeling experiments. A convenient and efficient route for the synthesis of 1,4‐diketones through the carbonyl‐oxygen‐assisted formal hydration of 4‐alkynones with complete regioselectivity was achieved under mild transition‐metal‐free conditions. The observed complete regioselectivity is supported by control and isotope‐labelling experiments.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800024