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Synfacts 2010(6): 0682-0682
DOI: 10.1055/s-0029-1219866
DOI: 10.1055/s-0029-1219866
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
A Concise Synthesis of (S)-β-Methylisoleucine
J. A. Pigza, T. F. Molinski*
University of California San Diego, La Jolla, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
20. Mai 2010 (online)
Significance
The SeO2-promoted oxidative rearrangement of 2-substituted oxazolines 2 into 3, followed by hydrogenation-hydrogenolysis, allows convenient access to chiral α-amino acids 4. Oxazinone 3 (R = H) can be viewed as a chiral glycine synthon. The authors reported a highly diastereoselective addition of dimethylallylstannane to the unsubstituted oxazinone (S)-3 under Brønsted acid catalysis. The product 5 can be efficiently converted into the highly branched amino acid l-β-methylisoleucine (6), an amino acid residue found in biologically active marine-derived peptides.