947601-81-2Relevant articles and documents
Synthesis of enantiopure 1,4-ethyl- and 1,4-ethylene-bridged cispentacin by lipase-catalyzed enantioselective ring opening of β-lactams
Forro, Eniko,Fueloep, Ferenc
, p. 573 - 575 (2007/10/03)
1,4-Ethyl- and 1,4-ethylene-bridged cispentacin enantiomers 1a, 1c and 2a, 2c were prepared through the lipase-catalyzed enantioselective ring opening of racemic exo-3-azatricyclo[4.2.1.02.5]nonan-4-one, (±)-1, and exo-3-azatricyclo[4.2.1.02.5]non-7-en-4-one, (±)-2. High enantioselectivity (E >200) was observed when the Lipolase-catalyzed reactions were performed with 1equiv of H2O in diisopropyl ether at 70°C. The resolved β-amino acids 1a and 2a (yield 46%) and β-lactams 1b and 2b (yield≥40%) could be easily separated. The ring opening of lactam enantiomers with 18% HCl afforded the corresponding β-amino acid hydrochloride enantiomers (ee ≥98%).