October 2013
Intermediate to advanced
242 pages
9h 22m
English
Content preview from Methods of Non-a-Amino Acid Synthesis, 2nd Edition
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116
Methods of Non-α-Amino Acid Synthesis, Second Edition
The desymmetrization of dimethyl 3-(benzylamino)glutarate (186) was accom-
plished via aminolysis using lipase B from Candida antarctica. Reaction with ben-
zylamine and the lipase B gave 187 in 92% yield.
104
This enantiopure product was
subsequently converted to 3,4-diaminobutanoic acid 188 in ve steps, as shown.
Hofmann rearrangement
105
of the amide to the amine was followed by deprotection,
which was complicated by lactam formation, requiring the nal acid hydrolysis
step. Other lipases resolved racemic methyl 3-tert-butoxycarbonylaminobutanoate
and allowed the isolation of (+)-methy ...
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