Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 35, Pages 4917-4925Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800917
Keywords
Bronsted acids; Lewis bases; [4+2] Annulation; Allenoates; Organocatalysis
Categories
Funding
- National Natural Science Foundation of China [21702189, 21672193, 21272218]
- China Postdoctoral Science Foundation [2017M610458, 2018T110737]
- Zhengzhou University of China
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The selective formation of an annulated 4H-pyran from an allenoate and an olefin demonstrated the dual roles of triethylenediamine (DABCO) in both Lewis base promoted [4 + 2] annulation and BrOnsted base mediated C=C isomerization. Interestingly, the role of the BrOnsted base could be quenched selectively with the presence of a BrOnsted acid (PhCO2H), and annulated 3,4-dihydro-2H-pyran was obtained as the major product.
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