Categories: C-C Bond Formation > Cyclic compounds > Cyclic ketones
Synthesis of cycloheptanones and higher homologues
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Recent Literature
A [6 + 2] annulation that involves the combination of β-alkenoyl acylsilanes
and a vinyllithium derivative enables in one operation and a stereoselective
manner the construction of eight-membered ring systems containing useful
functionalities for further synthetic elaboration from readily available six-
and two-carbon components.
K. Takeda, H. Haraguchi, Y. Okamoto, Org. Lett.,
2003, 5, 3705-3707.
The reaction of β-keto esters with CF3CO2ZnCH2I
provided the corresponding chain-extended products in moderate to good
yields. α-Substituted acyclic β-keto esters reacted less efficiently than
cyclic β-keto esters or simple β-keto esters.
S. Xue, Y.-K. Liu, L.-Z. Li, Q.-X. Guo, J. Org. Chem., 2005,
70, 8245-8247.
[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.
