title: Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer-supported triphenylphosphine: synthesis of protected (2S, 3S)-[3-(2)H, (15)N]-tyrosine.
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 (15)N-labeled (-)-8-phenylmenthylhippurate with R-(-)-4-triisopropylsilyloxybenzyl-α-d chloride.
authors.affiliation: Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, 43210, USA.
authors.forename: Derek W
authors.initials: DW
authors.lastname: Barnett
authors.forename: Maryanne S
authors.initials: MS
authors.lastname: Refaei
authors.forename: Robert W
authors.initials: RW
authors.lastname: Curley
mesh_terms: D000096:Acetone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D001592:Benzyl Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry*; D009587:Nitrogen Isotopes / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D011108:Polymers / Q000737:chemistry; D014443:Tyrosine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001592:Benzyl Alcohols; D001593:Benzyl Compounds; D009587:Nitrogen Isotopes; D009943:Organophosphorus Compounds; D011108:Polymers; D000096:Acetone; C061896:triphenylphosphine; D014443:Tyrosine; C021292:benzyl chloride; D003903:Deuterium; C032052:hexachloroacetone
keywords: alcohols; benzylic; chiral; chlorides; deuteration; tyrosine