Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer‐supported triphenylphosphine: synthesis of protected (2S, 3S)‐[3‐2H, 15N]‐tyrosine |
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| Authors: | Derek W. Barnett Maryanne S. Refaei Robert W. Curley Jr. |
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| Affiliation: | 1. Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, , Columbus, OH, 43210 USA;2. Ohio State Biochemistry Program, The Ohio State University, , Columbus, OH, 43210 USA |
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| 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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| Keywords: | chiral benzylic deuteration chlorides alcohols tyrosine |
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