Synthesis of optically active, unnatural α-substituted glutamic acid derivatives by a chiral calcium-catalyzed 1,4-addition reaction

Tetsu Tsubogo; Yuichiro Kano; Koki Ikemoto; Yasuhiro Yamashita; Sh Kobayashi

doi:10.1016/j.tetasy.2010.03.004

Synthesis of optically active, unnatural α-substituted glutamic acid derivatives by a chiral calcium-catalyzed 1,4-addition reaction

Tetsu Tsubogo, Yuichiro Kano, Koki Ikemoto, Yasuhiro Yamashita, Sh Kobayashi

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

32 Citations (Scopus)

Abstract

The first catalytic asymmetric 1,4-addition reactions of azlactones with acrylic esters have been developed. A chiral coordinative calcium catalyst was found to be effective for these reactions, and the desired 1,4-adducts were obtained in good yields and enantioselectivities. The product was converted to the corresponding α-alkylated glutamic acid by acid hydrolysis.

Original language	English
Pages (from-to)	1221-1225
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	21
Issue number	9-10
DOIs	https://doi.org/10.1016/j.tetasy.2010.03.004
Publication status	Published - 2010 May 17

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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abstract = "The first catalytic asymmetric 1,4-addition reactions of azlactones with acrylic esters have been developed. A chiral coordinative calcium catalyst was found to be effective for these reactions, and the desired 1,4-adducts were obtained in good yields and enantioselectivities. The product was converted to the corresponding α-alkylated glutamic acid by acid hydrolysis.",

author = "Tetsu Tsubogo and Yuichiro Kano and Koki Ikemoto and Yasuhiro Yamashita and Sh Kobayashi",

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AU - Tsubogo, Tetsu

AU - Kano, Yuichiro

AU - Ikemoto, Koki

AU - Yamashita, Yasuhiro

AU - Kobayashi, Sh

PY - 2010/5/17

Y1 - 2010/5/17

N2 - The first catalytic asymmetric 1,4-addition reactions of azlactones with acrylic esters have been developed. A chiral coordinative calcium catalyst was found to be effective for these reactions, and the desired 1,4-adducts were obtained in good yields and enantioselectivities. The product was converted to the corresponding α-alkylated glutamic acid by acid hydrolysis.

AB - The first catalytic asymmetric 1,4-addition reactions of azlactones with acrylic esters have been developed. A chiral coordinative calcium catalyst was found to be effective for these reactions, and the desired 1,4-adducts were obtained in good yields and enantioselectivities. The product was converted to the corresponding α-alkylated glutamic acid by acid hydrolysis.

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JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

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ER -

Synthesis of optically active, unnatural α-substituted glutamic acid derivatives by a chiral calcium-catalyzed 1,4-addition reaction

Abstract

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