88691-33-2

Upstream product

• 591-51-5 phenyllithium 
• 64715-63-5 (E)-(S)-N-(1-isopropyl-2-methoxyethyl)propylideneamine 
• 74-88-4 methyl iodide 
• 100-52-7 benzaldehyde 
• 64715-88-4 (S)-2-amino-1-methoxy-3-methylbutane 
• 925-90-6 ethylmagnesium bromide 
• 88691-30-9 N-benzylidene-O-methyl-L-valinol 
• 84983-97-1 N-benzylidene-L-valinol 

Relevant academic research and scientific papers

Asymmetric Reaction of Chiral Azomethines with Organometallic Reagents

Reaction of (E)-(S)-N-(1-isopropyl-2-methoxyethyl)benzylideneamine (2) with ethylmagnesium bromide gave a mixture of (1S,1'S)- and (1R,1'S)-N-(1'-isopropyl-2'-methoxyethyl)-1-phenylpropylamines (3) (91:9 percent). (E)-(S)-N-(1-Isopropyl-2-methoxyethyl)propylideneamine (5) was treated with phenyllithium to give (1R,1'S)- and (1S,1'S)-3 (95:5 percent).On the other hand, reaction of (E)-(S)-N-(2-hydroxy-1-isopropylethyl)benzylideneamine (6) with ethylmagnesium bromide yielded a mixture of (1S,1'S)- and (1R,1'S)-N-(2'-hydroxy-1'-isopropylethyl)-1-phenylpropylamines (7) (78:22 percent).The absolute configurations of these amines were determined by circular dichroism (CD) spectroscopy and comparison with authentic samples synthesized by alternative methods.Keyword -- absolute configuration; asymmetric reaction; chiral amine; chiral azomethine; Grignard reaction; N-methylation; (S)-N-methylvalinol; O-methylation; phenyllithium; phenylpropylamine