Alcohol from epoxides

Altylic alcohols from epoxides. Reaction of T with epoxides and then DBN gives reasonable yields of allylic alcohols as the t-butyldimethylsilyl ether. 

The use of a cationic aza-Cope rearrangement in concert with a Mannich cyclization has also been applied to the total synthesis of enantiomerically pure (—)-crinine (359) (205). In the event, nucleophilic opening of cyclopentenoxide with the aluminum amide that was formed on reaction of (/ )-a-methylbenzyl-amine and trimethylaluminum gave the amino alcohol 485 together with its (15,25) diastereomer. Although there was essentially no asymmetric induction in this process, the diastereomeric amino alcohols were readily separated by chromatography, and the overall procedure therefore constitutes an efficient means for the preparation of enantiomerically pure 2-amino alcohols from epoxides. When the hydrochloride salt derived from 485 was treated with paraformaldehyde and potassium cyanide, the amino nitrile 486 was formed. Subsequent Swem oxida-... 

Curini, M. Epifano, F. Marcotullio, M. C. Rosati, O. Zirconium sulfophenyl phospho-nate as a heterogeneous catalyst in the preparation of /1-amino alcohols from epoxides. Eur. J. Org. Chem. 2001, 4149-4152. 

Alcohols from epoxides. Free radical reaction using titanocene dichloride as an... 

Catalytic hydrogenolysis of C—O bonds of benzyl esters and similar compounds by deuterium has rarely been used for preparation of labeled compounds, whereas predeuterated Pd in D20 is recommended for formation of deuterated alcohols from epoxides.63... 

Diborane in tetrahydrofuran reduces epoxides, but the yields are low, and other products are formed by pathways that result from the electrophilic character of diborane/ Diborane reduction occurs in better yield in the presence of BH4, but the electrophilic role played by diborane is still evident because the dominant product is that resulting from addition of hydride at the more substituted carbon." Dissolving metals, particularly lithium in ethylenediamine, give synthetically useful yields of alcohols from epoxides/ ... 

Sources of Alcohols 615 Preparation of Alcohols by Reduction of Aldehydes and Ketones 617 Preparation of Alcohols by Reduction of Carboxylic Acids 620 Preparation of Alcohols from Epoxides 620... 

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