Combined application of organozinc chemistry and one-pot hydroboration-Suzuki coupling to the synthesis of amino acids.
Hydroboration using 9-BBN-H of the protected enantiomerically pure but-3-enylglycine derivative 11, prepared by copper-catalysed allylation of the serine-derived organozinc reagent 1, followed by Suzuki coupling of the derived borane with a variety of aromatic halides, 2-bromopyridine and 2-bromopropene gives the protected amino acids 14a-l and 15. This method augments our previous methods for the synthesis of phenylalanine homologues.
Rodríguez
Arantxa
A
Department of Chemistry, Dainton Building, University of Sheffield, Brook Hill, Sheffield, UK S3 7HF.
Miller
David D
DD
Jackson
Richard F
RF
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001959:Bromates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D008956:Models, Chemical; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000596:Amino Acids; D001959:Bromates; D009942:Organometallic Compounds; D015032:Zinc