78617-54-6

Upstream product

• 16369-05-4 valinol 
• 74-88-4 methyl iodide 
• 89876-70-0 (2S,1'S)-N,3-dimethyl-N'-1'-phenylethyl-2-hydrazinobutanol 
• 89876-71-1 (2S,1'S)-N,3-dimethyl-N'-1'-phenylpropyl-2-hydrazinobutanol 

Downstream Products

• 113336-48-4 N-(1-hydroxymethyl-2-methylpropyl)-N-methylbenzoylformamide 
• 113336-59-7 (R)-N-<(S)-1-hydroxymethyl-2-methylpropyl>N-methyl-mandelamide 
• 129087-37-2 (S)-4-2'-Hydroxy-1'-isopropyl-N-methylethylamino-1-phenylbutanone 
• 86553-16-4 (2S,4S)-2-(4-Chloro-phenyl)-4-isopropyl-3-methyl-oxazolidine 
• 86553-15-3 (2S,4S)-4-Isopropyl-3-methyl-2-phenyl-oxazolidine 
• 95421-92-4 (S)-ValNOP 
• 143490-19-1 (2S,4S)-2-(2-bromophenyl)-4-isopropyl-3-methyl-1,3-oxazolidine 
• 143490-19-1 (2R,4S)-2-(2-bromophenyl)-4-isopropyl-3-methyl-1,3-oxazolidine 
• 140424-70-0 (2S,4S)-o-<2-(4-isopropyl-N-methyl-1,3-oxazolidinyl)>benzaldehyde 
• 140424-71-1 (2R,4S)-o-<2-(4-isopropyl-N-methyl-1,3-oxazolidinyl)>benzaldehyde 
• 181205-63-0 (S)-5-isopropyl-4-methylmorpholine-2,3-dione 
• 93643-90-4 (1S,1'S)-1-cyclohexyl-N-2'-hydroxy-1'-isopropylethyl-N-methyl-2-phenylethylamine 
• 93643-91-5 (1S,1'S)-1-(3''-cyclohexenyl)-N-2'-hydroxy-1'-isopropylethyl-N-methyl-2-phenylethylamine 
• 89876-69-7 (E)-(S)-N'-benzylidene-N,3-dimethyl-2-hydrazinobutanol 

Relevant academic research and scientific papers

Diastereoselectivity of Organometallic Additions to Nitrones Bearing Sterogenic N-Substituents

The diastereoselectivity of organometallic additions to nitrones bearing stereogenic α-arylethyl, β-methoxyalkyl, and β-(silyloxy)alkyl substituents on nitrogen has been investigated.High and complementary diastereoselectivity (90-94percent) was observed in the additions of Grignard reagents to nitrones (e.g. 22 and 23) bearing the potentially chelating β-methoxyalkyl group.However, the opposite selectivity resulted from the reaction of methylmagnesium bromide with the corresponding silyl ether (27).The relative stereochemistry of selected hydroxylamine adducts wasestablished by reduction of their phosphate and carbonate derivatives to known amines (37a,b and 39), by periodate cleavage of a β-hydroxy hydroxylamine (41b), and by various correlations (Scheme II).The high facial diastereoselectivity observed with the N-(β-methoxyalkyl)nitrones is explained by a simple chelation model (Scheme III).

Alkylation of a Chiral Hydrazone by Means of Asymmetric Addition of Grignard Reagents to the Carbon-Nitrogen Double Bond

A chiral hydrazone, (E)-(S)-N'-benzylidene-N,3-dimethyl-2-hydrazinobutanol (6), was synthesized from (S)-valinol.Compound was reacted with Grignard reagents to give optically pure (2S,1'S)-N,3-dimethyl-N'-1'-phenylalkyl-2-hydrazinobutanols (7a and 7b).However, N'-2-aryl-1'-phenylethyl-N,3-dimethyl-2-hydrazinobutanols (7c and 7d) were each obtained as a mixture of two diastereomers.Nitrogen-nitrogen bonds of 7a and 7b were cleaved by hydrogenolysis to give (S)-1-phenylalkyamines (8a and 8b), and their absolute configurations and optical purities were confirmed.These reactions were assumed to proceed via the chelated six-membered ring intermediates.Keywords -- absolute configuration; asymmetric reaction; chelated intermediate; chiral hydrazine; chiral hydrazone; conformation control; l-ephedrine; Grignard reaction; stereoselectivity; (S)-valinol