A new method for the stereoselective synthesis of alpha-substituted serine amino acid analogues.
[reaction: see text]. A new method was developed for the stereoselective synthesis of alpha-substituted serine amino acids. The strategy utilizes a common enantiomerically enriched intermediate obtained through an enzymatic desymmetrization. A variety of amino acids were synthesized in good ee's through nucleophilic acetylide addition reactions and palladium-catalyzed Sonogashira couplings.
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
Jonathan W
JW
Lane
Randall L
RL
Halcomb
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D012694:Serine; D010165:Palladium