136120-93-9

Upstream product

• 44396-74-9 isobutylzinc iodide 
• 130115-37-6 (2R,3R,5R)-4-methyl-5-phenyl-3-(phenylthio)-2-morpholinol 

Downstream Products

• 136121-05-6 (R)-4-Methyl-2-(methyl-vinyloxycarbonyl-amino)-pentanoic acid 2-chloro-2-phenyl-ethyl ester 
• 130115-46-7 (3R,5R)-2,3,5,6-tetrahydro-3-i-butyl-5-phenyl-N-methyl-4H-1,4-oxazin-2-one 

Relevant academic research and scientific papers

Asymmetric synthesis of N-methyl-α-amino esters from a glyoxal derived chiral heterocycle

The reaction between a chiral template derived from glyoxal with organometallic reagents leads ultimately to the optically active title compounds. The stereochemical outcome of the key-step which involves substitution of a thiophenol group depends on the organometallic: predominantly inversion with alkyl copper or complete retention with alkyl zinc halides. The stereodirecting effect of an allylic hydroxy group in an iminium intermediate is evidenced in the case of the organozinc reagent.

A new chiral glycine-cation equivalent. Asymmetric synthesis of optically pure β-amino alcohols and α-amino esters

Reaction of organometallic reagents with a chiral glycine template derived from glyoxal serves as a key step in asymmetric syntheses of the title products.