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Studies on N ‐Activation for the Lipase‐Catalyzed Enantioselective Preparation of β‐Amino Esters from 4‐Phenylazetidin‐2‐one
Author(s) -
Sundell Riku,
Kanerva Liisa T.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403467
Subject(s) - chemistry , candida antarctica , lipase , enantioselective synthesis , enantiomer , methanol , enantiomeric excess , candida rugosa , organic chemistry , catalysis , reactivity (psychology) , triacylglycerol lipase , yield (engineering) , stereochemistry , enzyme , medicine , alternative medicine , pathology , materials science , metallurgy
The 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.