476013-32-8

Upstream product

• 100-52-7 benzaldehyde 
• 397332-07-9 (5S,6R)-4,5-dimethyl-6-phenyl-3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one 
• 397332-61-5 (5S,6R)-4,5-dimethyl-6-phenyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one 
• 67462-20-8 (1R,2S)-N-amino-2-methylamino-1-phenyl-1-propanol 
• 299-42-3 ephedrine 
• 1850-61-9 (1R,2S)-N-methyl-N-nitroso-2-amino-1-phenyl-1-propanol 

Downstream Products

• 76549-02-5 (-)-(2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoic acid 
• 397332-61-5 (5S,6R)-4,5-dimethyl-6-phenyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one 

Relevant academic research and scientific papers

An improved procedure for the asymmetric aldol reaction of the titanium enolate of an N3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one

The direct formation of the titanium enolate of N3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one has been achieved through complexation with titanium tetrachloride at 25°C, followed by deprotonation with triethylamine (-78 to 25°C). The preformed titanium enolate has been reacted with D2O/DCl to afford deuterated derivative 6 and also reacted with a series of aromatic and aliphatic aldehydes affording aldol adducts 4a-f with crude diastereoselectivities ranging from 8:1 to 38:1.

Toward the development of a structurally novel class of chiral auxiliaries: Diastereoselective Aldol reactions of a (1R,2S)-ephedrine-based 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one

(equation Presented) 8 examples Asymmetric aldol addition reactions have been conducted with (1R,2S)-ephedrine-derived 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one (2). Diastereoselectivities range from 75:25 to 99:1 for the formation of the crude non-Evan