Categories: C-C Bond Formation > Carbocyclic compounds > Cyclic enones
Synthesis of cycloheptenones and higher homologues
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Recent Literature
A palladium-catalyzed oxidative cross-coupling of vinyl boronic acids and cyclic
α-diazocarbonyl compounds enables an efficient synthesis of 1,3-diene compounds.
Mechanistically, the reaction involves migratory insertion of palladium carbene
as the key step.
Y. Xia, Y. Xia, Z. Liu, Y. Zhang, J. Wang, J. Org. Chem., 2014,
79, 7711-7717.
[ReBr(CO)3(thf)]2 catalyzes the reaction of a
1,3-dicarbonyl cyclic compound with an acetylene to give a medium-sized cyclic
compound in excellent yield. By using isocyanide as an additive, the insertion
of acetylenes into a carbon-carbon single bond occurs under mild conditions.
Y. Kuninobu, A. Kawata, K. Takai, J. Am. Chem. Soc., 2006, 128,
11368-11369.
An efficient and regioselective Yb(OTf)3-promoted palladium-catalyzed
oxidative cyclization of γ-heteroalkenyl β-keto amides has been developed. Under
simple aerobic condition, various six-, seven-, and eight-membered-ring N-
and O-heterocycles were obtained in excellent yield.
K.-T. Yip, J.-H. Li, O.-Y. Lee, D. Yang, Org. Lett., 2005, 7,
5717-5719.
Access to 2-Alkyltropones via Organic Base-Catalyzed Tandem Deamination and
Aldol Condensation of Tropinone-Derived Quaternary Ammonium Salts
Y. Wang, Q.-Q. Wu, S.-K. Tian, J. Org. Chem., 2023, 88,
16456-16466.