Diels-Alder cycloadditions of 3-phenylamino-5-bromo-2-pyrone for the synthesis of constrained α-amino acid derivatives

Won Suk Kim; Jin Hee Lee; Jongmin Kang; Cheon Gyu Cho

doi:10.1016/j.tetlet.2003.12.097

Diels-Alder cycloadditions of 3-phenylamino-5-bromo-2-pyrone for the synthesis of constrained α-amino acid derivatives

Won Suk Kim
, Jin Hee Lee
, Jongmin Kang
, Cheon Gyu Cho

Department of Chemistry & Nanoscience

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

22 Scopus citations

Abstract

3-Phenylamino-5-bromo-2-pyrone undergoes facile Diels-Alder cycloadditions with various electron deficient dienophiles to afford an array of functionally rich and stereochemically defined cycloadducts in good to excellent isolated yields. Due to the electron donacity of the amine group, it only proceeds in normal electron demand D-A cycloadditions. Subsequent ring openings with NaOMe provided constrained α-amino acid derivatives.

Original language	English
Pages (from-to)	1683-1687
Number of pages	5
Journal	Tetrahedron Letters
Volume	45
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2003.12.097
State	Published - 16 Feb 2004

Bibliographical note

Funding Information:
This work was supported by IMT-2000 Program of Ministry of Information & Communication, Korea. K.W.S. thanks BK21 program for the financial support.

Keywords

2-Pyrone
Constrained α-amino acid
Diels-Alder

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10.1016/j.tetlet.2003.12.097

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title = "Diels-Alder cycloadditions of 3-phenylamino-5-bromo-2-pyrone for the synthesis of constrained α-amino acid derivatives",

abstract = "3-Phenylamino-5-bromo-2-pyrone undergoes facile Diels-Alder cycloadditions with various electron deficient dienophiles to afford an array of functionally rich and stereochemically defined cycloadducts in good to excellent isolated yields. Due to the electron donacity of the amine group, it only proceeds in normal electron demand D-A cycloadditions. Subsequent ring openings with NaOMe provided constrained α-amino acid derivatives.",

keywords = "2-Pyrone, Constrained α-amino acid, Diels-Alder",

author = "Kim, \{Won Suk\} and Lee, \{Jin Hee\} and Jongmin Kang and Cho, \{Cheon Gyu\}",

note = "Funding Information: This work was supported by IMT-2000 Program of Ministry of Information \& Communication, Korea. K.W.S. thanks BK21 program for the financial support.",

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doi = "10.1016/j.tetlet.2003.12.097",

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T1 - Diels-Alder cycloadditions of 3-phenylamino-5-bromo-2-pyrone for the synthesis of constrained α-amino acid derivatives

AU - Kim, Won Suk

AU - Lee, Jin Hee

AU - Kang, Jongmin

AU - Cho, Cheon Gyu

N1 - Funding Information: This work was supported by IMT-2000 Program of Ministry of Information & Communication, Korea. K.W.S. thanks BK21 program for the financial support.

PY - 2004/2/16

Y1 - 2004/2/16

N2 - 3-Phenylamino-5-bromo-2-pyrone undergoes facile Diels-Alder cycloadditions with various electron deficient dienophiles to afford an array of functionally rich and stereochemically defined cycloadducts in good to excellent isolated yields. Due to the electron donacity of the amine group, it only proceeds in normal electron demand D-A cycloadditions. Subsequent ring openings with NaOMe provided constrained α-amino acid derivatives.

AB - 3-Phenylamino-5-bromo-2-pyrone undergoes facile Diels-Alder cycloadditions with various electron deficient dienophiles to afford an array of functionally rich and stereochemically defined cycloadducts in good to excellent isolated yields. Due to the electron donacity of the amine group, it only proceeds in normal electron demand D-A cycloadditions. Subsequent ring openings with NaOMe provided constrained α-amino acid derivatives.

KW - 2-Pyrone

KW - Constrained α-amino acid

KW - Diels-Alder

UR - https://www.scopus.com/pages/publications/0842305156

U2 - 10.1016/j.tetlet.2003.12.097

DO - 10.1016/j.tetlet.2003.12.097

M3 - Article

AN - SCOPUS:0842305156

SN - 0040-4039

VL - 45

SP - 1683

EP - 1687

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

Diels-Alder cycloadditions of 3-phenylamino-5-bromo-2-pyrone for the synthesis of constrained α-amino acid derivatives

Abstract

Bibliographical note

Keywords

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