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

doi:10.1016/S0040-4039(03)00002-9

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

16 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 language	English
Pages (from-to)	1611-1614
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(03)00002-9
Publication status	Published - 2003 Feb 17

Bibliographical note

Funding Information:
We thank the Center for Molecular Catalysis at Seoul National University through KOSEF and LGLS for generous financial support for this work. J.S.P. and C.E.Y. acknowledge the financial support in the form of BK21 fellowships.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(03)00002-9

Cite this

@article{3e86a8df8edb43c3b1d8b23111dc2df2,

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

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.",

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

note = "Funding Information: We thank the Center for Molecular Catalysis at Seoul National University through KOSEF and LGLS for generous financial support for this work. J.S.P. and C.E.Y. acknowledge the financial support in the form of BK21 fellowships.",

year = "2003",

month = feb,

day = "17",

doi = "10.1016/S0040-4039(03)00002-9",

language = "English",

volume = "44",

pages = "1611--1614",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "8",

}

TY - JOUR

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

N1 - Funding Information: We thank the Center for Molecular Catalysis at Seoul National University through KOSEF and LGLS for generous financial support for this work. J.S.P. and C.E.Y. acknowledge the financial support in the form of BK21 fellowships.

PY - 2003/2/17

Y1 - 2003/2/17

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0037450385&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037450385&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(03)00002-9

DO - 10.1016/S0040-4039(03)00002-9

M3 - Article

AN - SCOPUS:0037450385

SN - 0040-4039

VL - 44

SP - 1611

EP - 1614

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

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

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this