130115-48-9

Upstream product

• 130115-44-5 4-methyl-5-phenyl-3-propenyl-2-morpholinol 
• 1027825-29-1 (3R,5R)-3-Allyl-2-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-phenyl-morpholine 
• 130115-37-6 (2R,3R,5R)-4-methyl-5-phenyl-3-(phenylthio)-2-morpholinol 
• 84773-28-4 (R)-2-(methylamino)-2-phenylethanol 

Downstream Products

• 136121-07-8 (R)-2-(Methyl-vinyloxycarbonyl-amino)-pent-4-enoic acid 2-chloro-2-phenyl-ethyl ester 
• 136121-07-8 (S)-2-(Methyl-vinyloxycarbonyl-amino)-pent-4-enoic acid 2-chloro-2-phenyl-ethyl ester 

Relevant academic research and scientific papers

Kinetic resolution via the [2,3] stevens rearrangement of epimeric six-membered ammonium ylides: A new entry to enantio-enriched α-amino acid derivatives

The asymmetric [2,3] Stevens rearrangement of epimeric mixtures of N-allylic ammonium salts derived from (5R)-5-phenyl-1,4-oxazin-2-one is shown to proceed with efficient kinetic resolution to afford the unnatural α-amino acid derivatives in high enantio-

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.

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.