388579-13-3

Upstream product

• 98-88-4 benzoyl chloride 
• 388579-11-1 ethyl (2'S,2R,3R)-3-(1',4'-dioxaspiro[4,5]dec-2'-yl)aziridine-2-carboxylate 
• 112980-46-8 ethyl (2'S)-3-(1',4'-dioxa-spiro[4.5]dec-2'-yl)-acrylate 
• 388579-10-0 ethyl (2R)-2,3-dibromo-3-(1',4'-dioxaspiro[4,5]dec-2'-yl)propanoate 

Downstream Products

• 388579-14-4 ethyl (4S,5R)-4-{(2'S)-1',4'-dioxaspiro[4,5]dec-2'-yl}-2-phenyl-4,5-dihydro-1,3-oxazole-5-carboxylate 

Relevant academic research and scientific papers

The ring expansions of glyceraldehyde-derived aziridine-2-carboxylates to oxazolines take place with an uncommon regiochemistry

The ring expansion of the D-glyceraldehyde-derived ethyl trans-N-benzoylaziridine-2-carboxylate 9 occurs with retention of configuration, giving the ethyl trans-oxazoline-5-carboxylate 10 as the only product. The observed regioselectivity is rather unusual, since aziridine-2-carboxylates generally rearrange to give oxazoline-4-carboxylates. Conversely, the ring expansion of the cis-N-benzoyl compound 11 under the same reaction conditions is much slower and less stereoselective, giving a mixture of cis- and trans-oxazolines, but with the same regioselectivity. The hydrolysis of 10 under mild conditions permits the synthesis of the 3-amino-3-deoxy-D-xylonic acid derivative 13.