Abstract
AbstractThe effect of N‐substitution was examined for the enantioselective lipase‐catalyzed ring‐opening reaction of racemic 4‐phenylazetidin‐2‐one with methanol in dry organic solvents. Marked differences in the reactivity of various N‐protected 4‐phenylazetidin‐2‐ones were observed. Preparative‐scale reactions with Candida antarctica lipase B (Novozym 435 preparation) yielded N‐acylated methyl (R)‐3‐amino‐3‐phenylpropanoates with enantiomeric excess (ee) values >99 % in up to a 49 % isolated yield, whereas Thermomyces lanuginosus lipase (Lipozyme TM IM) gave enantiomerically enriched methyl (S)‐3‐acetamido‐3‐phenylpropanoate. Candida antarctica lipase A catalyzed the cleavage of the N‐chloroacetyl protective group, whereas all of the other examined lipases underwent the ring‐opening reaction.
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