Journal
CHEMICAL SCIENCE
Volume 12, Issue 27, Pages 9328-9332Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc02575a
Keywords
-
Categories
Funding
- European Union's Horizon 2020 research and innovation program [786976]
- Israel Science Foundation [330/17]
- European Research Council (ERC) [786976] Funding Source: European Research Council (ERC)
Ask authors/readers for more resources
The Cope rearrangement of 2,3-divinyloxiranes leads to the formation of 4,5-dihydrooxepines with two contiguous stereocenters, allowing for efficient synthesis of 1,6-dicarbonyl compounds through hydrolysis. Using an Ir-based catalyst enables excellent control over regio- and stereochemistry, providing a promising strategy for the synthesis of these compounds.
The Cope rearrangement of 2,3-divinyloxiranes, a rare example of epoxide C-C bond cleavage, results in 4,5-dihydrooxepines which are amenable to hydrolysis, furnishing 1,6-dicarbonyl compounds containing two contiguous stereocenters at the 3- and 4-positions. We employ an Ir-based alkene isomerization catalyst to form the reactive 2,3-divinyloxirane in situ with complete regio- and stereocontrol, which translates into excellent control over the stereochemistry of the resulting oxepines and ultimately to an attractive strategy towards 1,6-dicarbonyl compounds.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available