133625-99-7

Upstream product

• 132652-65-4 tert-butyl 2,2-dimethyl-4-[(E)-2-phenylethenyl]-1,3-oxazolane-3-carboxylate 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 100-39-0 benzyl bromide 
• 108-86-1 bromobenzene 
• 132682-25-8 (E)-(R)-(+)-3-(2'-phenyl-1'-ethylenyl)-2-oxazolidinone 
• 132639-29-3 tert-butyl 2,2-dimethyl-4-[(Z)-2-phenylethenyl]-1,3-oxazolane-3-carboxylate 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 709026-61-9 (E/Z)-(R)-N-Boc-2,2-dimethyl-4-(2-phenylethenyl)oxazolidine 

Downstream Products

• 116611-56-4 tert-butyl (R)-(1-hydroxy-4-phenylbutan-2-yl)carbamate 
• 321983-60-2 (4S,5S,6R)-4-hydroxymethyl-5-iodo-6-phenyl-1,3-oxazin-2-one 
• 100564-78-1 (2R)-(tert-butoxycarbonylamino)-4-phenylbutanoic acid 
• 674777-51-6 N-[(1S,2R,3S)-2-bromo-3-hydroxy-3-phenyl-1-[(R_S)-phenylsulfinylmethyl]propyl]-4-methyl-1-benzenesulfonamide 
• 674777-52-7 N-[(1S,2R,3S)-2-bromo-3-hydroxy-3-phenyl-1-[(S_S)-phenylsulfinylmethyl]propyl]-4-methyl-1-benzenesulfonamide 
• 674777-38-9 N-[(1R,2E)-3-phenyl-1-[(R_S)-phenylsulfinylmethyl]-2-propenyl]-4-methyl-1-benzenesulfonamide 
• 674777-37-8 N-[(1R,2E)-3-phenyl-1-[(S_S)-phenylsulfinylmethyl]-2-propenyl]-4-methyl-1-benzenesulfonamide 
• 674777-31-2 [(E)-(R)-1-((R)-Benzenesulfinylmethyl)-3-phenyl-allyl]-carbamic acid tert-butyl ester 
• 674777-28-7 [(E)-(R)-1-((S)-Benzenesulfinylmethyl)-3-phenyl-allyl]-carbamic acid tert-butyl ester 
• 674777-25-4 ((E)-(R)-3-Phenyl-1-phenylsulfanylmethyl-allyl)-carbamic acid tert-butyl ester 
• 674777-21-0 (E)-2-(tert-butyloxycarbonylamino)-4-phenyl-3-butenyl methanesulfonate 

Relevant academic research and scientific papers

Regio- and stereoselective synthesis of 1,3-aminoalcohol derivatives from allylamine derivatives via internal sulfinyl group participation

The regio- and stereoselective preparation of 1,3-aminoalcohol derivatives from protected allylamines via intramolecular participation by the sulfinyl group is reported. A carbamate protecting group on nitrogen leads to products arising from nucleophilic

Investigations of a nucleophilic alaninol synthon derived from serine

A nucleophilic synthon, (S)-(+)-4-(2-oxazolidonyl)-methyltriphenylphosphinyl iodide 6, available from L-serine in five steps (overall yield of 52%), reacts with aldehydes to produce alkenes in good to excellent yields (74-89%) and, in some cases, provides

Synthetic Elaboration of the Side Chain of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine: A New Regio- And Stereoselective Strategy to δ-Functionalized β-Amino Alcohols

An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)-ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an easy and mild procedure for the regio- and stereoselective synthesis of unsaturated amino alcohols.

Synthesis of Chiral Vinylglycines

(R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8.Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (>95percent ee) and double-bond geometry.D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives β,γ-unsaturated amino acids with the L configuration.The double-bond geometry is controlled by the nature of the phosphorous ylide employed.The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.