Cyclic ketals of tartaric acid: Simple and tunable reagents for the determination of the absolute configuration of primary amines

You Jin Shim, Kihang Choi

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

(Figure Presented) 2,2Diphenyl-[1,3]dioxolane-4,5-dicarboxylic acid (DPD) and 2,2-dinaphthalen-2-yl-[1,3]dioxolane-4,5-dicarboxylic acid (DND) have been synthesized starting from dimethyl tartrate. DPD and DND amides of α-chiral primary amines showed significantly different 1H chemical shift values depending on the stereochemistry of the derivatizing agent. On the basis of this chemical shift difference, the absolute configuration of amine substrates could be assigned. DND amides showed significantly larger chemical shift differences than the corresponding DPD amides allowing for a more error-free assignment.

Original languageEnglish
Pages (from-to)880-882
Number of pages3
JournalOrganic Letters
Volume12
Issue number4
DOIs
Publication statusPublished - 2010 Feb 19

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ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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