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Asymmetric Synthesis of β 2 ‐homo‐ tert ‐Leucine via Radical Addition to Enantiopure N ‐Fumaroylhexahydrobenzooxazolidin‐2‐one
Author(s) -
EscuderoCasao Margarita,
Juaristi Eusebio
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200448
Subject(s) - enantiopure drug , chemistry , hydrogenolysis , curtius rearrangement , peptidomimetic , regioselectivity , hydrolysis , stereochemistry , catalysis , leucine , amino acid , organic chemistry , enantioselective synthesis , peptide , biochemistry
β ‐Amino acids are key structural elements in unnatural peptides, peptidomimetics, and many other physiologically active compounds. In view of their importance, we have developed an efficient synthetic route that provides highly enantiomerically enriched ( R )‐ and ( S )‐H‐ β 2 ‐h t Leu‐OH via highly diastereo‐ and regioselective addition of tert ‐butyl radical to enantiomerically pure N ‐fumaroyloxazolidinones, followed by removal of the chiral auxiliary, Curtius rearrangement, ester hydrolysis, and catalytic hydrogenolysis.