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Synthesis of (saturated) alcohols

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Ionic liquids enhanced the nucleophilicity of water and reduced the formation of elimination products in the nucleophilic hydroxylation of alkyl halides. The reactivity of other nucleophiles such as alcohols, phenol, and acetic acid in an ionic liquid was also investigated.
D. W. Kim, D. J. Hong, J. W. Seo, H. S. Kim, H. K. Kim, C. E. Song, D. Y. Chi, J. Org. Chem., 2004, 69, 3186-3189.

Convenient methods for the preparation of stable and non-volatile mono- and dichloroborane adducts of dioxane from dioxane-BCl₃ and NaBH₄ in the presence of catalytic amounts of tri- or tetraglyme were developed. The dioxane-monochloroborane adduct hydroborates representative olefins cleanly and rapidly and lead to the corresponding alcohols in quantitative yields after oxidation.
J. V. B. Kanth, H. C. Brown, J. Org. Chem, 2001, 66, 5359-5365.

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A highly efficient dynamic kinetic resolution (DKR) of secondary alcohols at room temperature was developed. In situ racemization of substrates using a Ru catalyst and lipase-catalyzed acylation provides enantiopure products in high yields in very short reaction times. The use of isopropenyl acetate as the acyl donor makes the purification of the products very easy.
B. Martin-Matute, M. Edin, Krisztian Bogar, J.-E. Baeckvall, Angew. Chem. Int. Ed., 2004, 43, 6535-6539.