Abstract
The work describes fluorine-activated and N-Boc-activated β-lactams as acyl donors to N-nucleophiles in the presence of Burkholderia cepacia lipase (lipase PS-D). Fluorine activation at the β-lactam ring causes the ring to open in high enantioselectivity and allows the preparation of β-dipeptides and β-amino amides. In the case of N-Boc-activation, the chemical ring opening is significant. β-Dipeptide formation can then be considerably enhanced by the presence of lipase PS-D and/or by temperature.
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