136121-07-8

Upstream product

• 5130-24-5 Vinyl chloroformate 
• 130115-48-9 (3R,5R)-3-allyl-4-methyl-5-phenyl-morpholine-2-one 
• 130115-37-6 (2R,3R,5R)-4-methyl-5-phenyl-3-(phenylthio)-2-morpholinol 
• 130115-44-5 4-methyl-5-phenyl-3-propenyl-2-morpholinol 
• 130115-48-9 (3R,5R)-2,3,5,6-tetrahydro-3-propenyl-5-phenyl-N-methyl-4H-1,4-oxazin-2-one and (3S,5R)-2,3,5,6-tetrahydro-3-propenyl-5-phenyl-N-methyl-4H-1,4-oxazin-2-one 
• 1027825-29-1 (3R,5R)-3-Allyl-2-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-phenyl-morpholine 

Relevant academic research and scientific papers

Reactions of glyoxal-derived iminium ions with unsaturated silyl and silyloxy reagents

Iminium ions derived from a condensation of glyoxal and N-methyl (R)-phenylglycinol react with allylic silanes (trimethylallyl and trimethylmetallylsilanes) and enoxysilanes (2-trimethylsilyloxypropene and 2-trimethylsilyloxystyrene). These reactions proceed in a totally stereoselective way as evidenced by a chemical correlation and an X-Ray analysis of a compound related to both series of experiments.

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.