authors |
Sousa, JLC; Talhi, O; Mendes, RF; Paz, FAA; Bachari, K; Silva, AMS |
nationality |
International |
journal |
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
author keywords |
Oxygen heterocycles; Cyclopropanes; Small ring systems; Fused-ring systems; Michael addition; Cyclization |
keywords |
1,2,3-TRISUBSTITUTED CYCLOPROPANES; NATURAL-PRODUCTS; MIRC REACTIONS; DISCOVERY; ANALOGS; AGENTS |
abstract |
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. |
publisher |
WILEY-V C H VERLAG GMBH |
issn |
1434-193X |
year published |
2016 |
issue |
23 |
beginning page |
3949 |
ending page |
3958 |
digital object identifier (doi) |
10.1002/ejoc.201600413 |
web of science category |
Chemistry, Organic |
subject category |
Chemistry |
unique article identifier |
WOS:000382962700006
|
ciceco authors
impact metrics
journal analysis (jcr 2019):
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journal impact factor |
2.889 |
5 year journal impact factor |
2.53 |
category normalized journal impact factor percentile |
67.544 |
dimensions (citation analysis):
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altmetrics (social interaction):
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