Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer-supported triphenylphosphine: synthesis of protected (2S, 3S)-[3-2H, 15N]-tyrosine

Authors

  • Derek W. Barnett,

    1. Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA
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  • Maryanne S. Refaei,

    1. Ohio State Biochemistry Program, The Ohio State University, Columbus, OH, USA
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  • Robert W. Curley Jr.

    Corresponding author
    1. Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA
    • Ohio State Biochemistry Program, The Ohio State University, Columbus, OH, USA
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Correspondence to: Robert W. Curley, Jr., Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA.

E-mail: curley.1@osu.edu

Abstract

Chirally deuterated benzyl chlorides were prepared using novel, general hexachloroacetone/polymer-supported triphenylphosphine treatment of chirally deuterated benzyl alcohols. Doubly labeled protected tyrosine was obtained in 62% yield with 86% de at the α-carbon and 82% de at the β-carbon. Key in the synthesis was the alkylation of 15N-labeled (−)-8-phenylmenthylhippurate with R-(−)-4-triisopropylsilyloxybenzyl-α-d chloride.

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