208935-32-4

Upstream product

• 208935-22-2 (S)-3-Benzoyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-vinyl-oxazolidin-2-one 
• 482315-16-2 C₂₀H₃₁NO₄Si 
• 482315-18-4 N-[(1S)-2-hydroxy-1-(tert-butyldimethylsilanyloxymethyl)-3-butenyl]-benzamide 
• 503560-10-9 N-[2-(tert-butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-benzamide 

Downstream Products

• 497227-96-0 ((4S,5S)-2-Phenyl-5-vinyl-4,5-dihydro-oxazol-4-yl)-methanol 
• 502925-03-3 (4S,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-((Z)-pentadec-3-enyl)-2-phenyl-4,5-dihydro-oxazole 
• 502925-07-7 N-((1S,2S)-2-Hydroxy-1-hydroxymethyl-but-3-enyl)-benzamide 
• 764-22-7 (2S,3R)-2-amino-1,3-octadecanediol 
• 482315-14-0 (4R,5S)-2-Phenyl-5-vinyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 503560-09-6 3-((4S,trans)-4,5-dihydro-4-methyl-2-phenyloxazol-5-yl)-N-methoxy-N-methyl propionamide 
• 497227-89-1 (4S,5S)-4-Hydroxymethyl-2-phenyl-5-vinyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 1027989-75-8 (4S,5R)-5-Formyl-4-methoxymethoxymethyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 503560-12-1 3-(4-hydroxymethyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-propionamide 
• 497227-90-4 (4S,5S)-4-Methoxymethoxymethyl-2-phenyl-5-vinyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 503560-13-2 3-(4-iodomethyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-propionamide 
• 502925-08-8 N-[1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-but-3-enyl]-benzamide 
• 503560-07-4 (2E)-3-((4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazol-5-yl)-acrylic acid methyl ester 
• 497227-92-6 (3aS,6R,6aR)-6-((E)-3-Iodo-allyl)-3a-methoxymethoxymethyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one 

Relevant academic research and scientific papers

Stereoselective synthesis of (+)-spectaline

Our synthesis of (+)-spectaline revealed that the methodology involving diastereoselective palladium(0)-catalyzed oxazoline formation and intramolecular reductive amination by catalytic hydrogenation of an oxazoline is an effective method for the asymmetric synthesis of natural products possessing complex functionalized piperidine cores.

Total synthesis of myriocin

A concise, stereocontrolled synthesis of myriocin was achieved. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0), MgBr2-promoted allylic stannane addition, and palladium(0)-catalyzed coupling of a vinyl iodide with an organozinc reagent.

Total synthesis of sphingofungin F.

[reaction: see text] A concise, stereocontrolled synthesis of sphingofungin F was achieved. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0), MgBr(2)-promoted gamma-alkoxy allylic stannane addition, and palladium(0)-ca

Palladium-catalyzed formation and stereoselective isomerization of 5- vinyloxazolines. Application to the formal synthesis of (S,S)-4-amino-3- hydroxy-5-phenylpentanoic acid

Vinyloxazolidinones have been found to undergo Pd(0)-catalyzed ionization followed by loss of carbon dioxide and subsequent cyclization to form vinyloxazolines. The reaction occurred under mild conditions, and enhancement of diastereomeric ratios with chiral substrates was obtained. 4- Benzyl-5-vinyloxazoline prepared by this method has been utilized in the stereoselective synthesis of (S,S)-4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA).