42142-54-1

Upstream product

• 74-89-5 methylamine 
• 93-91-4 1-phenylbutan-1,3-dione 
• 14091-93-1 3-(methylamino)-1-phenylbut-2-en-1-one 
• 73406-38-9 cis-4-methyl-6-phenyltetrahydro-2H-1,3-oxazin-2-one 
• 25756-06-3 rac-1,3-syn-3-amino-1-phenylbutanol 
• 7064-06-4 3-methyl-5-phenyl-4,5-dihydroisoxazole 
• 73406-37-8 N-<(1R,3R)/(1S,2S)-3-Hydroxy-1-methyl-3-phenylpropyl>carbaminsaeure-ethylester 

Downstream Products

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

Relevant academic research and scientific papers

Stereoselective reduction of enaminones to syn γ-aminoalcohols

One-pot reduction of enaminones to syn γ-aminoalcohols can be efficiently performed by lithium borohydride in the presence of cerium chloride as Lewis acid. Selectivities are very good with respect to classical reduction method of these products.

Convenient Procedure for the Reduction of β-Enamino Ketones: Synthesis of γ-Amino Alcohols and Tetrahydro-1,3-oxazines

γ-Amino alcohols 3 can be easily synthesized in very good yields by reduction of enaminones 1 with Na in PrOH-tetrahydrofuran.The reaction is fast, easy to perform, inexpensive and the easily accesible starting materials provide a convenient entry to γ-amino alcohols.The relative configuration assignment of the diastereomeric γ-amino alcohols obtained has been established by 1H and 13C NMR studies and unequivocally assigned by their cyclic tetrahydro-1,3-oxazine derivatives 4.

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.