Pd-catalyzed stereospecific azide substitution of α,β- unsaturated γ,δ-epoxy esters with double inversion of configuration

Masaaki Miyashita; Taiku Mizutani; Genta Tadano; Yasuhiro Iwata; Masahiro Miyazawa; Keiji Tanino

doi:10.1002/anie.200500838

Pd-catalyzed stereospecific azide substitution of α,β- unsaturated γ,δ-epoxy esters with double inversion of configuration

Masaaki Miyashita^*, Taiku Mizutani, Genta Tadano, Yasuhiro Iwata, Masahiro Miyazawa, Keiji Tanino

^*Corresponding author for this work

Department of Chemistry

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

43 Scopus citations

Abstract

(Chemical Equation Presented) Acyclic, cyclic, and optically active unsaturated γ,δ-epoxy esters are employed in a highly stereoselective synthesis of functionalized amino alcohols, amino acids, and α,α-disubstituted amino acids. The key step of the reaction sequence is a double inversion of configuration (see scheme).

Original language	English
Pages (from-to)	5094-5097
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	32
DOIs	https://doi.org/10.1002/anie.200500838
State	Published - 2005/08/12

Keywords

Amino acids
Asymmetric synthesis
Azides
Epoxides
Palladium

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200500838

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title = "Pd-catalyzed stereospecific azide substitution of α,β- unsaturated γ,δ-epoxy esters with double inversion of configuration",

abstract = "(Chemical Equation Presented) Acyclic, cyclic, and optically active unsaturated γ,δ-epoxy esters are employed in a highly stereoselective synthesis of functionalized amino alcohols, amino acids, and α,α-disubstituted amino acids. The key step of the reaction sequence is a double inversion of configuration (see scheme).",

keywords = "Amino acids, Asymmetric synthesis, Azides, Epoxides, Palladium",

author = "Masaaki Miyashita and Taiku Mizutani and Genta Tadano and Yasuhiro Iwata and Masahiro Miyazawa and Keiji Tanino",

year = "2005",

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T1 - Pd-catalyzed stereospecific azide substitution of α,β- unsaturated γ,δ-epoxy esters with double inversion of configuration

AU - Miyashita, Masaaki

AU - Mizutani, Taiku

AU - Tadano, Genta

AU - Iwata, Yasuhiro

AU - Miyazawa, Masahiro

AU - Tanino, Keiji

PY - 2005/8/12

Y1 - 2005/8/12

N2 - (Chemical Equation Presented) Acyclic, cyclic, and optically active unsaturated γ,δ-epoxy esters are employed in a highly stereoselective synthesis of functionalized amino alcohols, amino acids, and α,α-disubstituted amino acids. The key step of the reaction sequence is a double inversion of configuration (see scheme).

AB - (Chemical Equation Presented) Acyclic, cyclic, and optically active unsaturated γ,δ-epoxy esters are employed in a highly stereoselective synthesis of functionalized amino alcohols, amino acids, and α,α-disubstituted amino acids. The key step of the reaction sequence is a double inversion of configuration (see scheme).

KW - Amino acids

KW - Asymmetric synthesis

KW - Azides

KW - Epoxides

KW - Palladium

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U2 - 10.1002/anie.200500838

DO - 10.1002/anie.200500838

M3 - 学術論文

C2 - 16021641

AN - SCOPUS:23944449030

SN - 1433-7851

VL - 44

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 32

ER -

Pd-catalyzed stereospecific azide substitution of α,β- unsaturated γ,δ-epoxy esters with double inversion of configuration

Abstract

Keywords

ASJC Scopus subject areas

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