Stereodivergent silver-catalyzed synthesis of pyroglutamic acid esters

Byungjun Kim; Yuna Song; Sarah Yunmi Lee

doi:10.1039/d1cc04875a

Stereodivergent silver-catalyzed synthesis of pyroglutamic acid esters

Byungjun Kim, Yuna Song, Sarah Yunmi Lee

Department of Chemistry

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

8 Citations (Scopus)

Abstract

We report here a silver-catalyzed method for the enantio- and diastereodivergent synthesis of chiral pyroglutamic acid esters with multiple stereocenters. This process proceeds through asymmetric conjugate addition of glycine imine esters to a broad range of β-substituted α,β-unsaturated perfluorophenyl esters followed by lactamization. By leveraging catalyst control and stereospecificity of the 1,4-addition process, all four product stereoisomers containing two adjacent stereocenters are accessible with high stereoselectivity.

Original language	English
Pages (from-to)	11052-11055
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	84
DOIs	https://doi.org/10.1039/d1cc04875a
Publication status	Published - 2021 Oct 28

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2021.

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d1cc04875a

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abstract = "We report here a silver-catalyzed method for the enantio- and diastereodivergent synthesis of chiral pyroglutamic acid esters with multiple stereocenters. This process proceeds through asymmetric conjugate addition of glycine imine esters to a broad range of β-substituted α,β-unsaturated perfluorophenyl esters followed by lactamization. By leveraging catalyst control and stereospecificity of the 1,4-addition process, all four product stereoisomers containing two adjacent stereocenters are accessible with high stereoselectivity.",

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AU - Song, Yuna

AU - Lee, Sarah Yunmi

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PY - 2021/10/28

Y1 - 2021/10/28

N2 - We report here a silver-catalyzed method for the enantio- and diastereodivergent synthesis of chiral pyroglutamic acid esters with multiple stereocenters. This process proceeds through asymmetric conjugate addition of glycine imine esters to a broad range of β-substituted α,β-unsaturated perfluorophenyl esters followed by lactamization. By leveraging catalyst control and stereospecificity of the 1,4-addition process, all four product stereoisomers containing two adjacent stereocenters are accessible with high stereoselectivity.

AB - We report here a silver-catalyzed method for the enantio- and diastereodivergent synthesis of chiral pyroglutamic acid esters with multiple stereocenters. This process proceeds through asymmetric conjugate addition of glycine imine esters to a broad range of β-substituted α,β-unsaturated perfluorophenyl esters followed by lactamization. By leveraging catalyst control and stereospecificity of the 1,4-addition process, all four product stereoisomers containing two adjacent stereocenters are accessible with high stereoselectivity.

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JO - Chemical Communications

JF - Chemical Communications

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ER -

Stereodivergent silver-catalyzed synthesis of pyroglutamic acid esters

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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