315718-89-9

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 188048-28-4 (2S,3S)-(3-(1-(benzyloxy)prop-2-en-2-yl)oxiran-2-yl)methanol 
• 4083-64-1 Tosyl isocyanate 
• 315718-83-3 (2S,3S)-2-(1-Benzyloxymethyl-vinyl)-3-(4-methoxy-benzyloxymethyl)-oxirane 

Downstream Products

• 315718-94-6 (4S,5R)-4-(1-benzyloxymethylvinyl)-5-(4-methoxybenzyloxymethyl)-oxazolidin-2-one 

Relevant academic research and scientific papers

A regio- and stereodivergent route to all isomers of vic-amino alcohols.

Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.

A regio-and stereodivergent synthesis of vic-amino alcohols

(Matrix presented) A regio-and stereodivergent synthesis of vic-amino alcohols starting from vinylepoxides is described. The developed strategy focuses on the propensity of vinylepoxides and vinylaziridines to be ring-opened at the allylic position by sui