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Synthesis of GABOB and GABOB‐Based Chiral Units Possessing Distinct Protecting Groups
Author(s) -
Ivšić Trpimir,
Dokli Irena,
Rimac Ana,
Hameršak Zdenko
Publication year - 2014
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.201301374
Subject(s) - chemistry , desymmetrization , chirality (physics) , protecting group , stereoselectivity , yield (engineering) , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , chiral anomaly , physics , alkyl , materials science , fermion , quantum mechanics , nambu–jona lasinio model , metallurgy
In addition to the varied biological activity of GABOB (4‐amino‐3‐hydroxybutanoic acid), the structure of its protected derivatives makes them interesting chiral intermediates for the synthesis of more complex compounds. A stereoselective route to GABOB derivatives with three different protecting groups is presented, using anhydride desymmetrization as a chirality‐inducing step. Selective removal of the protecting groups gave compounds with a free carboxylic acid or hydroxy group. Removal of all of the protecting groups allowed GABOB to be isolated in good yield and with excellent ee .
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