Categories: C-O Bond Formation >
Synthesis of 1,2-diols
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Recent Literature
Effective hydrolysis of epoxides and aziridines was conducted in water at 60 or
100°C. Other types of nucleophile such as amines, sodium azide, and thiophenol
could also efficiently open epoxides and aziridines in hot water. Hot water acts
as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.
Z. Whang, Y.-T. Cui, Z.-B. Xu, J. Qu, J. Org. Chem., 2008,
73, 2270-2274.
Epoxides can be opened under neutral conditions with alcohols and thiols in the
presence of a catalytic amount of erbium(III) triflate, affording the
corresponding β-alkoxy alcohols and β-hydroxy sulfides in high yields. In water,
epoxide ring opening occurs to produce the corresponding diols in good yields.
R. Dalpozzo, M. Nardi, M. Oliverio, R. Paonessa, A. Procopio, Synthesis, 2009,
3433-3438.
Epoxides undergo rapid ring opening with a range of alcohols in the presence of
catalytic amount of carbon tetrabromide under mild and convenient conditions to
afford the corresponding β-alkoxy alcohols and 1,2-diols in high yields with
high regioselectivity.
J. S. Yadav, B. V. S. Reddy, K. Harikishan, Ch. Madan, A. V. Narsaiah,
Synthesis, 2005, 2897-2900.
Epoxides can be cleaved in a regio- and stereoselective manner under
neutral conditions with water, alcohols and acetic acid in the presence of
catalytic amounts of decatungstocerate(IV) ion, affording the corresponding
diols, β-alkoxy and β-acetoxy alcohols in high yields.
V. Mirkhani, S. Tangestaninejad, B. Yadollahi, L. Alipanah, Tetrahedron,
2003, 59, 8213-8218.
Lithiated epoxides react stereospecifically with boronates to give syn-1,2-diols,
a process that can be used iteratively to create triols containing four
stereogenic centers.
E. Vedrenne, O. A. Wallner, M. Vitale, F. Schmidt, V. K. Aggarwal, Org. Lett., 2009,
11, 165-168.
Transformation of epoxides to β-alkoxy alcohols, acetonides, and α-alkoxy
ketones is achieved by using molybdenum(VI) dichloride dioxide (MoO2Cl2)
as a catalyst. Alcohol, aldehyde, oxime, tosyl, and tert-butyldimethylsilyl
functional groups are tolerated during the methanolysis and acetonidation of the
functionalized epoxides.
K. Jeyakumar, D. K. Chand, Synthesis, 2008,
807-819.
A very efficient and highly regioselective ring-opening reaction of epoxides
with benzoic acid and its derivatives in the presence of cat. amount of
tetrabutylammonium bromide (TBAB) in anhydrous acetonitrile gave selectively
protected diols.
A. Khalafi-Nezhad, M. N. Soltani Rad, A. Khoshnood, Synthesis,
2003, 2552-2558.
The reaction of chiral 1-aminoalkylepoxides with CO2, generated from
acidic treatment of an aqueous solution of NaHCO3 at room temperature,
efficiently afforded enantiopure cyclic carbonates with total selectivity.
Carbonates were readily transformed into the corresponding diols by reaction
with LiAlH4 or by basic hydrolysis.
J. M. Concellón, V. del Solar, S. Carcía-Granda, M. R. Díaz, J. Org. Chem.,
2007,
72, 7567-7568.
