73406-38-9

Upstream product

• 89762-93-6 syn-3-benzyloxyimino-1-phenyl-1-butanol 
• 89762-98-1 anti-3-benzyloxyimino-1-phenyl-1-butanol 
• 7064-06-4 3-methyl-5-phenyl-4,5-dihydroisoxazole 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 25756-06-3 rac-1,3-syn-3-amino-1-phenylbutanol 
• 105-58-8 Diethyl carbonate 
• 25756-06-3 3-amino-1-phenyl-1-butanol 

Downstream Products

• 42142-54-1 erythro-3-Methylamino-1-phenyl-butanol 
• 73406-39-0 c-4-Methyl-c-6-phenyl-r-2-(4-nitrophenyl)tetrahydro-1,3-oxazin 

Relevant academic research and scientific papers

Stereoselective Preparation of Acyclic syn-β-Amino Alcohols from β-Hydroxy Ketones via the Corresponding O-Benzyl Oximes

Reduction of β-hydroxy ketone O-benzyl oximes with lithium aluminum hydride in the presence of sodium or potassium methoxide afforded the corresponding syn-β-amino alcohols in highly stereoselective manner.A lythraceae alkaloid, lasubine II, was synthesiz

STEREOSELECTIVE PREPARATION OF ACYCLIC syn-1,3-AMINO ALCOHOLS FROM β-HYDROXY KETONES

syn-1,3-Amino alcohols are prepared in good yields by the stereoselective reduction of β-hydroxy-ketone-O-benzyloximes derived from acyclic β-hydroxy ketones with lithium aluminium hydride.

Synthesis via Isoxazolines, 5. - 1,3-Asymmetric Induction in the reduction of 3,5-Disubstituted 2-Isoxazolines; Diastereoselective Synthesis and Configurational Assignment of γ-Amino Alcohols

The cycloaddition of nitrile oxides to alkenes, followed by reduction of the ensuing 2-isoxazolines 3, yields γ-amino alcohols 4 in a regioselective manner.The stereoselectivity of the reduction step is examined; it is highest with LiAlH4 as the reducing agent. 1,3-Asymmetric induction by isoxazoline ring substituents leads to β-4:α-4 ratios of ca. 85:15 for 5-methyl and ca. 95:5 for 5-phenyl. (CH3)2S-BH3, less selectively, furnishes 60:40, Na-Hg and Na/ethanol reduction give rise to 40:60 diastereomer mixtures.From these, two amino alcohols of the α-series are isolated. 3a is reduced by NaBH3CN to give cis/trans-isoxazolines 11. - The relative configurations of β- and α-4 and, consequently, the steric course of these reductions, are established by 1H- and 13C-NMR studies of 4 as well as of cyclic derivatives (azetidine 7, tetrahydro-1,3-oxazine 10).In addition, conformations of the free amino alcohols 4 are suggested on the basis of 13C-NMR data.