期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 28, 页码 5469-5474出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100780
关键词
Oxygen heterocycles; Electrocyclic reactions; Substituent effects; Knoevenagel condensation; Endoperoxides
资金
- Ministry of Education, Culture, Sports, Science and Technology (MEXT)
- Okayama University
A facile access to 2,3,6-trisubstituted 2H-pyran-5-carboxylates is developed by employing 2-alkyl-2-enals as reactants with acetoacetates. The reaction involves Knoevenagel condensation followed by a 6 pi-electrocyclization, in which the presence of the C2 alkyl substituent in the enals favors the formation of (E)-Knoevenagel adducts for the ensuing electrocyclization. The resulting 2H-pyrans are hydrogenated to form 3,4-dihydro-2H-pyrans and converted into the endoperoxides by singlet-oxygen cycloaddition.
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