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http://hdl.handle.net/10773/20116
Título: | Catalytic One-Pot Diastereoselective Michael-Initiated Ring-Closure of Methyl Ketones with 3-Bromochromones: Synthesis of Cyclopropa[b]chromanones |
Autor: | Sousa, Joana L. C. Talhi, Oualid Mendes, Ricardo F. Almeida Paz, Filipe A. Bachari, Khaldoun Silva, Artur M. S. |
Palavras-chave: | 1,2,3-TRISUBSTITUTED CYCLOPROPANES NATURAL-PRODUCTS MIRC REACTIONS DISCOVERY ANALOGS AGENTS |
Data: | 2016 |
Editora: | WILEY-V C H VERLAG GMBH |
Resumo: | A one-pot diastereoselective base-catalyzed Michael-initiated ring-closure (MIRC) of activated methyl ketones with 3-bromochromones to give cyclopropa[b]chromanones is described. Three asymmetric centres are generated in the new cyclopropa[b]chromanone skeleton. Stereochemistry studies based on NMR spectroscopy and single-crystal X-ray diffraction analysis revealed the trans configuration of the cyclopropane ring, with the (1R,1aS,7aR)/(1S,1aR,7aS) pair of enantiomers, as was further confirmed by chiral HPLC. The use of acetone in our reaction produced a 1-acetyl-substituted cyclopropa[b]chromanone that can undergo a subsequent MIRC reaction with a second molecule of 3-bromochromone to give the first described 1,1-carbonylbis(cyclopropa[b]chromanone) dimers as a meso form. |
Peer review: | yes |
URI: | http://hdl.handle.net/10773/20116 |
DOI: | 10.1002/ejoc.201600413 |
ISSN: | 1434-193X |
Versão do Editor: | 10.1002/ejoc.201600413 |
Aparece nas coleções: | CICECO - Artigos |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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Catalytic One-Pot Diastereoselective Michael-Initiated Ring-Closure of Methyl Ketones with 3-Bromochromones Synthesis of Cyclopropa[b]chromanones_10.1002ejoc.201600413.pdf | 755.74 kB | Adobe PDF |
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