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Diastereospecific Synthesis of Vicinally Substituted 2-Oxazolidinones via Oxidative Rearrangement of α,β-Unsaturated γ-Lactams

Lidskog, Anna LU ; Li, Yutang LU ; Gupta, Arvind Kumar LU ; Mishra, Abhishek LU ; Sundin, Anders LU and Wärnmark, Kenneth LU (2025) In Journal of Organic Chemistry 90(2). p.1209-1213
Abstract

A diastereospecific synthesis of vicinally substituted 2-oxazolidinones from α,β-unsaturated lactams using m-chloroperoxybenzoic acid is reported. Several highly substituted 2-oxazolidinones were obtained in 19-46% yields in a one-pot reaction with complete control over the relative stereochemistry. The proposed reaction sequence consists of a Baeyer-Villiger oxidation, an epoxidation, and a concerted rearrangement. Experimental results and density functional theory calculations indicate that a CH2COOEt substituent at position 4 of the lactam is necessary for the diastereospecific rearrangement to take place.

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author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
90
issue
2
pages
5 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:85214380345
  • pmid:39762143
ISSN
0022-3263
DOI
10.1021/acs.joc.4c02653
language
English
LU publication?
yes
id
8fa1106b-73b8-46bd-9cfd-28dfe5ac45bd
date added to LUP
2025-03-19 10:16:56
date last changed
2025-06-11 16:25:11
@article{8fa1106b-73b8-46bd-9cfd-28dfe5ac45bd,
  abstract     = {{<p>A diastereospecific synthesis of vicinally substituted 2-oxazolidinones from α,β-unsaturated lactams using m-chloroperoxybenzoic acid is reported. Several highly substituted 2-oxazolidinones were obtained in 19-46% yields in a one-pot reaction with complete control over the relative stereochemistry. The proposed reaction sequence consists of a Baeyer-Villiger oxidation, an epoxidation, and a concerted rearrangement. Experimental results and density functional theory calculations indicate that a CH<sub>2</sub>COOEt substituent at position 4 of the lactam is necessary for the diastereospecific rearrangement to take place.</p>}},
  author       = {{Lidskog, Anna and Li, Yutang and Gupta, Arvind Kumar and Mishra, Abhishek and Sundin, Anders and Wärnmark, Kenneth}},
  issn         = {{0022-3263}},
  language     = {{eng}},
  month        = {{01}},
  number       = {{2}},
  pages        = {{1209--1213}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of Organic Chemistry}},
  title        = {{Diastereospecific Synthesis of Vicinally Substituted 2-Oxazolidinones via Oxidative Rearrangement of α,β-Unsaturated γ-Lactams}},
  url          = {{http://dx.doi.org/10.1021/acs.joc.4c02653}},
  doi          = {{10.1021/acs.joc.4c02653}},
  volume       = {{90}},
  year         = {{2025}},
}