Other Subjects
Full Access
ChemInform Abstract: Baker′s Yeast Reduction of 5-Acetyl-2-isoxazolines. Synthesis of Enantiomerically Pure 2,3-Dihydroxy Ketones and 1,2,4-Triols.
First published: May 30, 1989
Abstract
The 5-acetyl-2-isoxazolines (III), obtained by 1,3-dipolar ccloaddition reaction of the nitril oxides (I) with methyl vinyl ketone (II), are selectively reduced in the presence of bakers' yeast to form the diastereomeric alcohols (IV) and (V).
ChemInform Abstract
The 5-acetyl-2-isoxazolines (III), obtained by 1,3-dipolar ccloaddition reaction of the nitril oxides (I) with methyl vinyl ketone (II), are selectively reduced in the presence of bakers' yeast to form the diastereomeric alcohols (IV) and (V). Hydrogenolysis of (IV) produces the dihydroxy ketones (VI). (VIb) is further converted to the triol derivatives (VII). Analogous conversions of (V) are described in the original paper.
