Abstract
An efficient organocatalytic cascade reaction for synthesising functionalized bicyclic nitrones is reported. The reaction of dielectrophilic ethyl 2-(nitromethylene)-4-arylbut-3-ynoate and (E)-diethyl 2-((2-hydroxybenzylidene)-amino)malonates to give a unique nitrone scaffold in the presence of a catalytic amount of DABCO is described. The working mechanism was proposed to proceed with allene formation followed by intramolecular cyclization and the rearrangement of an oxygen atom in the nitro group. A broad range of substrates was accessed in this facile chemical transformation, in which the bicyclic nitrones were isolated in moderate to good yields (19% to 79%) with excellent diastereoselectivity (>20:1 dr). (Figure presented.).
Original language | English |
---|---|
Pages (from-to) | 170-175 |
Number of pages | 6 |
Journal | Advanced Synthesis and Catalysis |
Volume | 361 |
Issue number | 1 |
DOIs | |
Publication status | Published - 2019 Jan 11 |
Keywords
- 1-Nitro-1,3-Enynes
- Allene
- Bicyclic nitrones
- Rearrangement
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Fingerprint
Dive into the research topics of 'An Unprecedented Organocascade Synthesis of Functionalized Bicyclic Nitrones from 2-Aminomalonate Derived Nucleophiles and 1-Nitro-1,3-Enynes via Allenes Formation and Subsequent Rearrangement'. Together they form a unique fingerprint.Datasets
-
CCDC 1837750: Experimental Crystal Structure Determination
Huang, W.-Y. (Creator), Gurubrahamam, R. (Creator) & Chen, K. (Creator), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1zpb88, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1zpb88&sid=DataCite
Dataset