Deuterio compounds alcohols

Lithium tetradeuteridoaluminate Alcohols from carboxylic acid esters Deuterio compounds... 

Berkessel and Sklorz screened a variety of potential co-ligands for the Mn-tmtacn/H202 catalyzed epoxidation reaction and found that ascorbic acid was the most efficient one. With this activator the authors could oxidize the terminal olefins 1-octene and methyl acrylate with full conversion and yields of 83% and 97%, respectively, employing less than 0.1% of the metal complex (Scheme 86). Furthermore, with E- and Z-l-deuterio-1-octene as substrates, it was shown that the oxygen transfer proceeded stereoselectively with almost complete retention of configuration (94 2%). Besides the epoxidation, also the oxidation of alcohols to carbonyl compounds could be catalyzed by this catalytic system (see also Section in.C). 

Optically active primary-1-deuterio alcohols are important class of compounds, as these have been extensively studied for mechanistic studies of chemical and biochemical reactions [1]. However, their preparations are tedious or inefficient [2]. The preparation of these alcohols generally involves the fermenting yeast reduction of the corresponding deuterated aldehydes. Although high optical purity is achieved, the process is tedious and not amenable to large-scale preparation. 

Treating the dimethylaminodioxolan (631) with feebly acidic compounds ranging from t-butyl alcohol to acetic acid generates a series of simple aliphatic enols, e.g. (632) and (633), which are surprisingly stable, especially in DMSO solution. The deuterio-enols are even more stable. ... 

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