Efficient enantioselective synthesis of condensed and aromatic-ring-substituted tyrosine derivatives.
An efficient access to both condensed and conjugated tyrosine analogues of high enantiomeric purity is described. Novel ring-substituted tyrosines were synthesized by Suzuki cross couplings of appropriately protected l-3-iodotyrosine with a series of activated and deactivated boronic acid derivatives to achieve the target compounds in high yields. d- and l-4-hydroxy-1-naphthylalanines were readily prepared from the corresponding alpha-enamide in two different approaches, by asymmetric hydrogenation as well as by unselective hydrogenation and enzymatic resolution of the racemic mixture.
Knör
Sebastian
S
Lehrstuhl II für Organische Chemie, Department Chemie, Technische Universität München, Lichtenbergstrasse 4, Garching D-85747, Germany.
Laufer
Burkhardt
B
Kessler
Horst
H
D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D007470:Monoiodotyrosine / Q000737:chemistry; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D014443:Tyrosine; D007470:Monoiodotyrosine