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Categories: C-C Bond Formation > Oxygen-containing molecules > Alcohols >

Synthesis of alcohols

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Grignard Reaction


Hosomi-Sakurai Reaction


Recent Literature


β-Alkylation of various secondary alcohols with primary alcohols has been achieved in the presence of [Cp*IrCl2]2 (Cp* = pentamethylcyclopentadienyl) catalyst and a base. This reaction proceeds in good to excellent yield via successive hydrogen-transfer reactions and aldol condensation.
K.-I. Fujita, C. Asai, T. Yamaguchi, F. Hanasaka, R. Yamaguchi, Org. Lett., 2005, 7, 4017-4019.


An asymmetric α-alkylative reduction of prochiral ketones with primary alcohols has been disclosed. The reaction is catalyzed by both iridium and ruthenium complexes and gave optically active alcohols with elongation of the carbon skeleton with high enantioselectivity.
G. Onodera, Y. Nishibayashi, S. Uemura, Angew. Chem. Int. Ed., 2006, 45, 3819-3822.


A simple method for the chemo- and regioselective, direct catalytic allylic alkylation of aldehydes and cyclic ketones has been developed. The combination of palladium and enamine catalysis furnished α-allylic alkylated aldehydes and cyclic ketones in high yields.
I. Ibrahem, A. Córdova, Angew. Chem. Int. Ed., 2006, 45, 1952-1956.


A one-pot alkylation-silylation reaction of various epoxides with R3Al-R'3SiOTf occurs stereospecifically to give the corresponding alkylation-silylation products in excellent yields.
P. Shanmugam, M. Miyashita, Org. Lett., 2003, 3265-3268.


The reaction of dianions, derived from the reductive opening of phthalan (n=1) or isochroman (n=2) with lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB) at 0°C, with several epoxides gave 1,6- and 1,7-diols, respectively.
M. Yus, T. Soler, F. Foubelo, Tetrahedron, 2002, 58, 7009-7016.