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Synlett 1996; 1996(6): 519-520
DOI: 10.1055/s-1996-5490
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A Stereocontrolled Synthesis of Protected (2R,3R)-3-Mercaptoaspartic Acid via a β-Aspartyl Enolate Sulfenylation

Norio Shibata, Jack E. Baldwin* , Adam Jacobs, Mark E. Wood
  • *The Dyson Perrins Laboratory and the Oxford Centre for Molecular Sciences, South Parks Road, Oxford, OX1 3QY, U.K.
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Publication Date:
31 December 2000 (online)

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The unnatural α-amino acid (2R, 3R)-3-mercaptoaspartic acid was prepared stereoselectively in protected form (15) via electrophilic sulfenylation of a β-aspartate dianion2. A novel sulfenylating agent, 2,4-dimethoxybenzylthio-4-methylphenyl sulfonate (12) was developed and an application of (15) in the preparation of a tripeptide was investigated.

(2R, 3R)-3-mercaptoaspartic acid - β-aspartyl enolate - electrophilic sulfenylating agent - 2,4-dimethoxybenzylthio-4-methylphenyl sulfonate

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