Diastereospecific Synthesis of Vicinally Substituted 2-Oxazolidinones via Oxidative Rearrangement of α,β-Unsaturated γ-Lactams
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| Title: | Diastereospecific Synthesis of Vicinally Substituted 2-Oxazolidinones via Oxidative Rearrangement of α,β-Unsaturated γ-Lactams |
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| Authors: | Lidskog, Anna, Li, Yutang, Gupta, Arvind Kumar, Mishra, Abhishek, Sundin, Anders, Wärnmark, Kenneth |
| Contributors: | Lund University, Faculty of Science, Department of Chemistry, Centre for Analysis and Synthesis, Lunds universitet, Naturvetenskapliga fakulteten, Kemiska institutionen, Centrum för analys och syntes, Originator, Lund University, Profile areas and other strong research environments, Lund University Profile areas, LU Profile Area: Light and Materials, Lunds universitet, Profilområden och andra starka forskningsmiljöer, Lunds universitets profilområden, LU profilområde: Ljus och material, Originator, Lund University, Faculty of Engineering, LTH, LTH Profile areas, LTH Profile Area: Nanoscience and Semiconductor Technology, Lunds universitet, Lunds Tekniska Högskola, LTH profilområden, LTH profilområde: Nanovetenskap och halvledarteknologi, Originator, Lund University, Profile areas and other strong research environments, Strategic research areas (SRA), NanoLund: Centre for Nanoscience, Lunds universitet, Profilområden och andra starka forskningsmiljöer, Strategiska forskningsområden (SFO), NanoLund: Centre for Nanoscience, Originator |
| Source: | Journal of Organic Chemistry. 90(2):1209-1213 |
| Subject Terms: | Natural Sciences, Chemical Sciences, Organic Chemistry, Naturvetenskap, Kemi, Organisk kemi |
| Description: | 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. |
| Access URL: | https://doi.org/10.1021/acs.joc.4c02653 |
| Database: | SwePub |
Nájsť tento článok vo Web of Science | 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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| ISSN: | 00223263 15206904 |
| DOI: | 10.1021/acs.joc.4c02653 |