Abstract
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[4.2.1.0 2.5]nonan-4-one, (±)− 1 , and exo-3-azatricyclo[4.2.1.0 2.5]non-7-en-4-one, (±)− 2 . High enantioselectivity ( E>200) was observed when the Lipolase-catalyzed reactions were performed with 1 equiv of H 2O 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%).
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