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

2 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

Funding Information:
This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT & Future Planning (2021R1A2C4001752).

Publisher Copyright:
© The Royal Society of Chemistry 2021.

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/d1cc04875a

Cite this

@article{57d30a4c775f48bc9a13623fa148b10f,

title = "Stereodivergent silver-catalyzed synthesis of pyroglutamic acid esters",

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.",

author = "Byungjun Kim and Yuna Song and Lee, {Sarah Yunmi}",

note = "Funding Information: This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT & Future Planning (2021R1A2C4001752). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

year = "2021",

month = oct,

day = "28",

doi = "10.1039/d1cc04875a",

language = "English",

volume = "57",

pages = "11052--11055",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "84",

}

TY - JOUR

T1 - Stereodivergent silver-catalyzed synthesis of pyroglutamic acid esters

AU - Kim, Byungjun

AU - Song, Yuna

AU - Lee, Sarah Yunmi

N1 - Funding Information: This work was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT & Future Planning (2021R1A2C4001752). Publisher Copyright: © The Royal Society of Chemistry 2021.

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.

UR - http://www.scopus.com/inward/record.url?scp=85117892724&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85117892724&partnerID=8YFLogxK

U2 - 10.1039/d1cc04875a

DO - 10.1039/d1cc04875a

M3 - Article

C2 - 34608900

AN - SCOPUS:85117892724

SN - 1359-7345

VL - 57

SP - 11052

EP - 11055

JO - Chemical Communications

JF - Chemical Communications

IS - 84

ER -

Stereodivergent silver-catalyzed synthesis of pyroglutamic acid esters

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this