1294444-87-3

Upstream product

• 110-44-1 sorbic Acid 
• 1294444-86-2 tert-butyl (2R,3R,4S,5S,αR)-2,4,5-trihydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]hexanoate 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 38235-77-7 (R)-N-benzyl-1-phenylethylamine 
• 100-52-7 benzaldehyde 
• 81838-85-9 tert-butyl (2E,4E)-2,4-hexadienoate 
• 487042-22-8 (4E,2R,3R,αR)-tert-butyl 2-hydroxy-3-(N-benzyl-N-α-methylbenzylamino)hex-4-enoate 

Relevant academic research and scientific papers

Highly diastereoselective and stereodivergent dihydroxylations of acyclic allylic amines: Application to the asymmetric synthesis of 3,6-dideoxy-3-amino- l-talose

Aminohydroxylation of tert-butyl sorbate [tert-butyl (E,E)-hexa-2,4- dienoate] using enantiopure lithium (R)-N-benzyl-N-(α-methylbenzyl)amide and (-)-camphorsulfonyloxaziridine gives tert-butyl (R,R,R,E)-2-hydroxy-3-[N- benzyl-N-(α-methylbenzyl)amino]hex-4-enoate in >99:1 dr. Subsequent dihydroxylation under Upjohn conditions (OsO4/NMO) gives tert-butyl (2R,3R,4S,5S,αR)-2,4,5-trihydroxy-3-[N-benzyl-N-(α-methylbenzyl) amino]hexanoate (in 95:5 dr) while dihydroxylation under Donohoe conditions (OsO4/TMEDA) proceeds with antipodal diastereofacial selectivity to give the (R,R,R,R,R)-diastereoisomer (in 95:5 dr). The amino triols resulting from these dihydroxylation reactions are useful for further elaboration, as demonstrated by the asymmetric synthesis of 3,6-dideoxy-3-amino-l-talose.