Regioselective and stereoselective nucleophilic ring opening reactions of a phenyl-substituted aziridine: enantioselective synthesis of beta-substituted tryptophan, cysteine, and serine derivatives.
The asymmetric synthesis of beta-phenyl-substituted cysteine, tryptophan, and serine derivatives was successfully developed. In this approach, the key intermediate, enantiomerically pure 3-phenylaziridine-2-carboxylic ester 7, was prepared from alpha,beta-unsaturated ester 1 by employing the Sharpless asymmetric dihydroxylation. The aziridine 7 was treated with 4-methoxybenzylthiol, indole, and acetic acid to give beta-phenyl-substituted cysteine, tryptophan, and serine, respectively, in a clean S(N)2 type ring opening at the C3 position. This general approach can be used to synthesize a variety of beta-substituted novel amino acids.
Xiong
Chiyi
C
Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
Wang
Wei
W
Cai
Chaozhong
C
Hruby
Victor J
VJ
D000596:Amino Acids / Q000138:chemical synthesis; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D002855:Chromatography, Thin Layer; D003500:Cyclization; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010649:Phenylalanine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D001388:Aziridines; D001555:Benzene Derivatives; D012694:Serine; D010649:Phenylalanine; D014364:Tryptophan; D003545:Cysteine