A general asymmetric synthesis of syn- and anti-beta-substituted cysteine and serine derivatives.
A stereodivergent synthetic route has been developed to make the optically pure anti- and syn-beta-substituted cysteine and serine derivatives. In this approach, the key intermediates, > 94% enantiomerically pure cyclic sulfates 3 and aziridines 7, were prepared from alpha,beta-unsaturated esters 1, employing the Sharpless asymmetric dihydroxylation. The high regio- and stereoselective ring-opening reactions of cyclic sulfates and aziridines provided enantiomerically pure beta-substituted cysteine and serine derivatives.
Xiong
Chiyi
C
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
Wang
Wei
W
Hruby
Victor J
VJ
D000595:Amino Acid Sequence; D001388:Aziridines / Q000138:chemical synthesis; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013431:Sulfates / Q000138:chemical synthesis
D001388:Aziridines; D004952:Esters; D013431:Sulfates; D012694:Serine; D003545:Cysteine