An efficient synthesis of 3(S)-aminopiperidine-5(R)-carboxylic acid as a cyclic β,γ′-diamino acid

Jin Seong Park, Chang Eun Yeom, Soo Hyuk Choi, Yong Shik Ahn, Sunggu Ro, Young Ho Jeon, Dong Kyu Shin, B. Moon Kim

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

An orthogonally protected β,γ′-diamino acid 6 possessing conformationally-constrained ring system was synthesized as a novel cyclic amino acid analogue. This synthesis involves as key steps chemoselective enzymatic hydrolysis of cis-piperidine-3,5-dicarboxylic ester derivative followed by efficient kinetic resolution of the partially resolved half-acid to afford the C1-symmetric piperidine-3,5-dicarboxylic acid monoester in high enantiomeric excess (>98% ee). The optically active half-acid was transformed to the cyclic amino acid via Curtius-type rearrangement.

Original languageEnglish
Pages (from-to)1611-1614
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number8
DOIs
Publication statusPublished - 2003 Feb 17

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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