166582-12-3

Upstream product

• 145694-42-4 (S)-(+)-2-hydroxymethyl-3,3-dimethyl-4-phenyl-2-azetidinone 
• 7486-93-3 3,3-dimethyl-4-phenylazetidin-2-one 
• 145774-30-7 1-hydroxymethyl-3,3-dimethyl-4-phenyl-2-azetidinone 

Relevant academic research and scientific papers

Switchover of the diastereoselectivity induced by a simple selection of titanium(IV) halides in the addition reaction of silyl ketene acetals to a chiral imine

Switchover of the diastereoselectivity was recognized by a simple selection of titanium(IV) halides in the reaction of silyl ketene acetal with a chiral imine possessing a derivative of D-(-)-phenylglycine as an auxiliary. TiF4 effected the formation of (3S)-β-amino ester, while TiCl4 gave (3R)-isomer. The β-amino esters thus obtained were convened into the corresponding β-lactams on treatment with Me3Al without loss of the stereochemical integrity.

Convenient syntheses of optically active β-lactams by enzymatic resolution

Optically active β-lactams were synthesized by lipase-catalyzed kinetic resolution using the enantioselective hydrolysis of N-acyloxymethyl β- lactams (3) in an organic solvent and the transesterification of N- hydroxymethyl β-lactams (2) with vinyl aceta