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

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Cyclic Amino Acids
Carboxylic Acids
Acids
Dicarboxylic Acids
Enzymatic hydrolysis
Esters
Hydrolysis
Derivatives
Kinetics
piperidine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Park, Jin Seong ; Yeom, Chang Eun ; Choi, Soo Hyuk ; Ahn, Yong Shik ; Ro, Sunggu ; Jeon, Young Ho ; Shin, Dong Kyu ; Kim, B. Moon. / An efficient synthesis of 3(S)-aminopiperidine-5(R)-carboxylic acid as a cyclic β,γ′-diamino acid. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 8. pp. 1611-1614.
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An efficient synthesis of 3(S)-aminopiperidine-5(R)-carboxylic acid as a cyclic β,γ′-diamino acid. / Park, Jin Seong; Yeom, Chang Eun; Choi, Soo Hyuk; Ahn, Yong Shik; Ro, Sunggu; Jeon, Young Ho; Shin, Dong Kyu; Kim, B. Moon.

In: Tetrahedron Letters, Vol. 44, No. 8, 17.02.2003, p. 1611-1614.

Research output: Contribution to journalArticle

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T1 - An efficient synthesis of 3(S)-aminopiperidine-5(R)-carboxylic acid as a cyclic β,γ′-diamino acid

AU - Park, Jin Seong

AU - Yeom, Chang Eun

AU - Choi, Soo Hyuk

AU - Ahn, Yong Shik

AU - Ro, Sunggu

AU - Jeon, Young Ho

AU - Shin, Dong Kyu

AU - Kim, B. Moon

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AB - 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.

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