771479-08-4

Upstream product

• 74-85-1 ethene 

Downstream Products

• 771479-09-5 (1'R)-3-(1',2'-dibenzyloxyethyl)-4,5-dihydro-1,2-oxazole 
• 773091-81-9 (1'R)-3-(1'-benzyloxy-2'-hydroxyethyl)-2-methyl-4,5-dihydro-1,2-oxazolium tetrafluoroborate 

Relevant academic research and scientific papers

Isoxazolinium salts in asymmetric synthesis. 1. Stereoselective reduction induced by a 3′-alkoxy stereocentre. A new approach to polyfunctionalized β-amino acids

A new approach to optically active N-methylamino acids is presented, relying on stereoselective reduction of N-methylisoxazolinium salts with a dioxyethyl side-chain. The diastereoselectivity of the reduction step is studied systematically, in comparison with that of respective isoxazolines. A two-step transformation of isoxazolinium salts - with NaBH3(OAc) and subsequent catalytic hydrogenation as well as a one-pot reduction by catalytic hydrogenation led to high (95:5 and 87:13) diastereomeric ratios of protected erythro-N-methylaminopentanetriols. The hydroxyethyl side-chain is elaborated by oxidation to afford the β-N-methylamino acid 37, exemplifying the potential of this strategy.