A FACILE METHOD FOR THE STEREOSELECTIVE PREPARATION OF ACYCLIC syn-1,3-AMINO ALCOHOLS FROM β-HYDROXY KETONES
- 5 December 1984
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 13 (12) , 2065-2068
- https://doi.org/10.1246/cl.1984.2065
Abstract
Treatment of acyclic β-hydroxy ketones with O-benzylhydroxylamine hydrochloride gave a mixture of stereoisomers of the corresponding O-benzyloximes. The mixture of the both isomers was reduced with lithium aluminum hydride in the presence of sodium or potassium methoxide to afford syn-1,3-amino alcohols in a highly stereoselective manner.This publication has 3 references indexed in Scilit:
- Stereochemistry of nucleophilic addition to cyclohexanone. The importance of two-electron stabilizing interactionsJournal of the American Chemical Society, 1981
- Mechanism of lithium aluminum hydride reduction of ketones. Kinetics of reduction of mesityl phenyl ketoneJournal of the American Chemical Society, 1976
- Reduction of oximes, oxime ethers, and oxime esters with diborane. Novel synthesis of aminesThe Journal of Organic Chemistry, 1969