Ring-opening of oxazolines derived from l-serine: a short and efficient stereoselective synthesis of all four diastereomers of 3-mercaptoaspartic acid derivatives

Sang Hyeup Lee; Juhan Bok; Xin Qi; Sook Kyung Kim; Yoon Sik Lee; Juyoung Yoon

doi:10.1016/j.tetlet.2007.08.041

Ring-opening of oxazolines derived from l-serine: a short and efficient stereoselective synthesis of all four diastereomers of 3-mercaptoaspartic acid derivatives

Sang Hyeup Lee, Juhan Bok, Xin Qi, Sook Kyung Kim, Yoon Sik Lee, Juyoung Yoon

Department of Chemistry & Nanoscience

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

13 Scopus citations

Abstract

Facile methods are described for accessing four diastereomerically pure 3-mercaptoaspartic acid derivative from l-aspartic acid. In our synthesis, ring-opening reactions of oxazoline-4,5-dicarboxylate with thiolacetic acid as well as the stereochemical interconversion of both α- and β-configuration via oxazoline chemistry were utilized as key steps.

Original language	English
Pages (from-to)	7309-7312
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	41
DOIs	https://doi.org/10.1016/j.tetlet.2007.08.041
State	Published - 8 Oct 2007

Bibliographical note

Funding Information:
This work was supported by the SRC program of the Korea Science and Engineering Foundation (KOSEF) (R11-2005-008-02001-0), the Korea Research Foundation Grant (KRF-2004-005-C00093) and the research grant from KRIBB Research Initiative Program, Korea.

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title = "Ring-opening of oxazolines derived from l-serine: a short and efficient stereoselective synthesis of all four diastereomers of 3-mercaptoaspartic acid derivatives",

abstract = "Facile methods are described for accessing four diastereomerically pure 3-mercaptoaspartic acid derivative from l-aspartic acid. In our synthesis, ring-opening reactions of oxazoline-4,5-dicarboxylate with thiolacetic acid as well as the stereochemical interconversion of both α- and β-configuration via oxazoline chemistry were utilized as key steps.",

author = "Lee, {Sang Hyeup} and Juhan Bok and Xin Qi and Kim, {Sook Kyung} and Lee, {Yoon Sik} and Juyoung Yoon",

note = "Funding Information: This work was supported by the SRC program of the Korea Science and Engineering Foundation (KOSEF) (R11-2005-008-02001-0), the Korea Research Foundation Grant (KRF-2004-005-C00093) and the research grant from KRIBB Research Initiative Program, Korea. ",

year = "2007",

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doi = "10.1016/j.tetlet.2007.08.041",

language = "English",

volume = "48",

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journal = "Tetrahedron Letters",

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T1 - Ring-opening of oxazolines derived from l-serine

T2 - a short and efficient stereoselective synthesis of all four diastereomers of 3-mercaptoaspartic acid derivatives

AU - Lee, Sang Hyeup

AU - Bok, Juhan

AU - Qi, Xin

AU - Kim, Sook Kyung

AU - Lee, Yoon Sik

AU - Yoon, Juyoung

N1 - Funding Information: This work was supported by the SRC program of the Korea Science and Engineering Foundation (KOSEF) (R11-2005-008-02001-0), the Korea Research Foundation Grant (KRF-2004-005-C00093) and the research grant from KRIBB Research Initiative Program, Korea.

PY - 2007/10/8

Y1 - 2007/10/8

N2 - Facile methods are described for accessing four diastereomerically pure 3-mercaptoaspartic acid derivative from l-aspartic acid. In our synthesis, ring-opening reactions of oxazoline-4,5-dicarboxylate with thiolacetic acid as well as the stereochemical interconversion of both α- and β-configuration via oxazoline chemistry were utilized as key steps.

AB - Facile methods are described for accessing four diastereomerically pure 3-mercaptoaspartic acid derivative from l-aspartic acid. In our synthesis, ring-opening reactions of oxazoline-4,5-dicarboxylate with thiolacetic acid as well as the stereochemical interconversion of both α- and β-configuration via oxazoline chemistry were utilized as key steps.

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DO - 10.1016/j.tetlet.2007.08.041

M3 - Article

AN - SCOPUS:34548500781

SN - 0040-4039

VL - 48

SP - 7309

EP - 7312

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

Ring-opening of oxazolines derived from l-serine: a short and efficient stereoselective synthesis of all four diastereomers of 3-mercaptoaspartic acid derivatives

Abstract

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