Highly functionalized organolithium reagents for enantiomerically pure alpha-amino acid synthesis.
[reaction: see text] Highly functionalized l-serine-derived organolithium reagents have been generated and reacted with a variety of electrophiles, delivering novel enantiomerically pure adducts. These adducts were then converted into homochiral amino alcohols and novel nonproteinogenic alpha-amino acids, including an aspartic acid mimic that has been synthesized in an enantiomerically pure form for the first time.
Kenworthy
Martin N
MN
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
Kilburn
John Paul
JP
Taylor
Richard J K
RJ
D000596:Amino Acids / Q000138:chemical synthesis*; D001224:Aspartic Acid / Q000138:chemical synthesis; D007202:Indicators and Reagents; D018020:Lithium Compounds / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D012694:Serine / Q000737:chemistry*
D000596:Amino Acids; D007202:Indicators and Reagents; D018020:Lithium Compounds; D009942:Organometallic Compounds; D001224:Aspartic Acid; D012694:Serine