454451-67-3

Upstream product

• 595582-07-3 1-(2-hydroxy-(1S)-phenyl-ethyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester 
• 20989-17-7 (2S)-2-phenylglycinol 
• 105-45-3 acetoacetic acid methyl ester 
• 120417-13-2 (S)-2-(tert-butyldimethylsilyloxy)-1-phenylethylamine 
• 814-68-6 acryloyl chloride 
• 476187-10-7 (Z)-3-((S)-2-Hydroxy-1-phenyl-ethylamino)-but-2-enoic acid methyl ester 

Downstream Products

• 476187-19-6 (1S)-(2S)-(3S)-1-(2-hydroxy-1-phenyl-ethyl)-2-methyl-piperidine-3-carboxylic acid methyl ester 
• 1864003-05-3 (2S,3S)-2-Methyl-piperidine-3-carboxylic acid methyl ester 
• 454451-70-8 (3S)-(8R)-(8aR)-methyl-5-oxo-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-8-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Asymmetric synthesis of nitrogen heterocycles by reaction of chiral β-enaminocarbonyl substrates with acrylate derivatives

We have studied the reactivity of β-enaminoesters 1 (R2=OMe) or β-enaminoketone 1 (R2=Me), derived from (S)-phenylglycinol, with activated acrylate derivatives. Substrates 1 (R1=Me) afforded by aza-annulation oxazololactam

Enantioselective synthesis of indolizidine and quinolizidine derivatives from chiral non-racemic bicyclic lactams

Chiral non-racemic bicyclic lactams 2b,c, derived from (R)- and (S)-phenylglycinol, were used in the enantioselective synthesis of (-)-lupinine and 5-epitashiromine, respectively. The efficiency of the synthesis relied on the high diastereoselectivities of formation and reduction of compounds 2b,c.

A novel stereocontrolled synthesis of enantiopure bicyclic lactams

A study on the reactivity of 3,4-dihydro-2-pyridones 9, derived from (S)-phenylglycinol, toward different bases is presented. Using a catalytic amount of bases, the cis bicyclic lactams were obtained with excellent diastereoselectivities.

Synthesis of enantiopure cis- and trans-2,3-disubstituted piperidines

The synthesis of enantiopure cis- and trans-2,3-disubstituted piperidines 4 is described. The key step of the synthesis involves the stereoselective reduction of chiral nonracemic lactams 2 by using BH3·Me2S. A rationalization of the stereoselectivity is presented.