Categories: C-C Bond Formation > Cyclic compounds > Cyclic alcohols
Synthesis of cyclopropanols
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Name Reactions
Recent Literature
1-Substituted cyclopropanols are formed in high yields in the
titanium(IV)isopropoxide-catalyzed reaction of esters with ethylmagnesium
bromide.
O. G. Kulinkovich, S. V. Sviridov, D. A. Vasilevski, Synthesis, 1991,
234.
The Kulinkovich reaction can be carried out successfully on lactones or
THP-protected hydroxy esters to give cyclopropyl diols.
A. Esposito, M. Taddei, J. Org. Chem., 2000,
65, 9245-9248.
A diastereofacial selective attack of epoxy ketones by bis(iodozincio)methane
leads to 2-(1-hydroxyalkyl)-1-alkylcyclopropanols in good yields. The dizinc
reagent, which acts as an effective bidentate Lewis acid, is easily prepared
from diiodomethane and zinc powder.
K. Nomura, K. Oshima, S. Matsubara, Angew. Chem., 2005, 117,
6010-6013.
A sequence of two gold(I)-catalyzed isomerization steps allows the synthesis of
functionalized acetoxy bicyclo[3.1.0]hexenes from 5-en-2-yn-1-yl acetates.
Acetoxy bicyclo[3.1.0]hexene products can be further transformed to
2-cycloalkenones by simple methanolysis.
A. Buzas, F. Gagosz, J. Am. Chem. Soc., 2006, 128,
12614-12615.
Regioselective dichlorocyclopropanation of 2-silyloxydienes furnishes
vinylcyclopropanol silyl ethers in good yield. Treatment with silver(I) at room
temperature effects disrotatory electrocyclic opening to a
2-chloro-3-silyloxypentadienyl cation, which then undergoes a Nazarov reaction
to provide chlorocyclopentenones.
T. N. Grant, F. G. West, J. Am. Chem. Soc., 2006, 128,
9348-9349.
