Categories: C-C Bond Formation > Carbocyclic compounds > Cyclic alcohols
Synthesis of cyclopropanols
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Recent Literature
The reaction of bimetallic CH2(ZnI)2 with α-chloroaldehydes
enables a diastereoselective synthesis of trans-2-substituted cyclopropanols in
very good yields and dr’s. The high trans-selectivity
resulted from equilibration of the cyclopropoxide intermediates.
K. Cheng, P. J. Carroll, P. J. Walsh, Org. Lett., 2011,
13, 2346-2349.
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 addition of diverse organometallic reagents to
1-phenylsulfonylcyclopropanols enables a simple and high-yielding synthesis of
1-substituted cyclopropanols. The transformation is amenable to sp-, sp2-,
or sp3-hybridized organometallic C-nucleophiles under mild conditions,
and the use of enantioenriched substrates led to highly diastereoselective
additions.
R. M. Rivera, Y. Jang, C. M. Poteat, V. N. G. Lindsay,
Org. Lett., 2020, 22, 6510-6515.
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.
Hydroboration of 1-alkynyl-1-boronate esters and in situ transmetalation
furnishes 1-alkenyl-1,1-borozinc heterobimetallic intermediates. Reaction with
aldehydes and in situ cyclopropanation generates B(pin) substituted cyclopropyl
carbinols with excellent diastereoselectivities. Oxidation provides
trisubstituted α-hydroxycyclopropyl carbinols, that allow access to both cis-
and trans-2,3-disubstituted cyclobutanones via a facile pinacol-type
rearrangement.
M. M. Hussain, H. Li, N. Hussain, M. Ureņa, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2009,
131, 6516-6524.
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. Int. Ed., 2005,
44, 5860-5863.
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.