Unusual selectivity in the ring-opening of γ-valerolactone oxide by amines

Zahra Mazloomi; Fabian Kallmeier; Sarah Kirchhecker; Bernhard M. Stadler; Swechchha Pandey; Claas Schünemann; Anke Spannenberg; Christian Hering-Junghans; Sergey Tin; Johannes G. de Vries; Eszter Baráth

doi:10.1039/d3cc01957h

Unusual selectivity in the ring-opening of γ-valerolactone oxide by amines

Zahra Mazloomi
, Fabian Kallmeier
, Sarah Kirchhecker
, Bernhard M. Stadler
, Swechchha Pandey
, Claas Schünemann
, Anke Spannenberg
, Christian Hering-Junghans
, Sergey Tin
, Johannes G. de Vries^*
, Eszter Baráth^*

^*Corresponding author for this work

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

1 Citation (Scopus)

Abstract

Primary and secondary amines selectively react with the lactone moiety of γ-valerolactone oxide (GVLO). Several primary amines afforded the resulting epoxyamides with an intact epoxy group. In some cases addition of two equivalents of amine resulted in additional epoxide opening to give α,γ-dihydroxy-β-amino-amides. The selective lactone-opening in GVLO was further corroborated by DFT-studies.

Original language	English
Pages (from-to)	8444-8447
Number of pages	4
Journal	Chemical Communications
Volume	59
Issue number	54
DOIs	https://doi.org/10.1039/d3cc01957h
Publication status	Published - 13 Jun 2023
Externally published	Yes

Access to Document

10.1039/d3cc01957h

Cite this

@article{884aa06adf3048059e7389e8139cafe4,

title = "Unusual selectivity in the ring-opening of γ-valerolactone oxide by amines",

abstract = "Primary and secondary amines selectively react with the lactone moiety of γ-valerolactone oxide (GVLO). Several primary amines afforded the resulting epoxyamides with an intact epoxy group. In some cases addition of two equivalents of amine resulted in additional epoxide opening to give α,γ-dihydroxy-β-amino-amides. The selective lactone-opening in GVLO was further corroborated by DFT-studies.",

author = "Zahra Mazloomi and Fabian Kallmeier and Sarah Kirchhecker and Stadler, \{Bernhard M.\} and Swechchha Pandey and Claas Sch{\"u}nemann and Anke Spannenberg and Christian Hering-Junghans and Sergey Tin and \{de Vries\}, \{Johannes G.\} and Eszter Bar{\'a}th",

note = "Publisher Copyright: {\textcopyright} 2023 The Royal Society of Chemistry.",

year = "2023",

month = jun,

day = "13",

doi = "10.1039/d3cc01957h",

language = "English",

volume = "59",

pages = "8444--8447",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "54",

}

TY - JOUR

T1 - Unusual selectivity in the ring-opening of γ-valerolactone oxide by amines

AU - Mazloomi, Zahra

AU - Kallmeier, Fabian

AU - Kirchhecker, Sarah

AU - Stadler, Bernhard M.

AU - Pandey, Swechchha

AU - Schünemann, Claas

AU - Spannenberg, Anke

AU - Hering-Junghans, Christian

AU - Tin, Sergey

AU - de Vries, Johannes G.

AU - Baráth, Eszter

PY - 2023/6/13

Y1 - 2023/6/13

N2 - Primary and secondary amines selectively react with the lactone moiety of γ-valerolactone oxide (GVLO). Several primary amines afforded the resulting epoxyamides with an intact epoxy group. In some cases addition of two equivalents of amine resulted in additional epoxide opening to give α,γ-dihydroxy-β-amino-amides. The selective lactone-opening in GVLO was further corroborated by DFT-studies.

AB - Primary and secondary amines selectively react with the lactone moiety of γ-valerolactone oxide (GVLO). Several primary amines afforded the resulting epoxyamides with an intact epoxy group. In some cases addition of two equivalents of amine resulted in additional epoxide opening to give α,γ-dihydroxy-β-amino-amides. The selective lactone-opening in GVLO was further corroborated by DFT-studies.

UR - https://www.scopus.com/pages/publications/85163975548

U2 - 10.1039/d3cc01957h

DO - 10.1039/d3cc01957h

M3 - Article

C2 - 37337749

AN - SCOPUS:85163975548

SN - 1359-7345

VL - 59

SP - 8444

EP - 8447

JO - Chemical Communications

JF - Chemical Communications

IS - 54

ER -

Unusual selectivity in the ring-opening of γ-valerolactone oxide by amines

Abstract

Access to Document

Other files and links

Fingerprint

Cite this