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A Tandem Iridium-Catalyzed 'Chain-Walking'/Cope Rearrangement Sequence
- Source :
- ACS Catalysis
- Publication Year :
- 2019
-
Abstract
- An iridium-catalyzed tandem olefin migration/Cope rearrangement of alkenyl ω-ene cyclopropanes is reported. By this means, a variety of complex annulenes are obtained as single diastereomers starting from cyclopropyl ester derived from simple 1,ω-dienes and alkenyldiazo compounds. Long-range olefin migration over up to 10 positions could be realized and coupled with an efficient Cope rearrangement to yield valuable scaffolds. Various functional groups are well-tolerated, giving rise to densely functionalized products. Furthermore, the present methodology could be successfully extended to yield bicyclic cycloheptenones starting from readily available alkenyl cyclopropanols via a Kulinkovich reaction.
- Subjects :
- Olefin fiber
Letter
Tandem
Kulinkovich reaction
Bicyclic molecule
iridium catalysis
010405 organic chemistry
Chemistry
General Chemistry
Annulene
010402 general chemistry
chain-walking remote functionalization iridium catalysis Cope rearrangement alkenyl cyclopropane
chain-walking
01 natural sciences
Combinatorial chemistry
Catalysis
0104 chemical sciences
Cope rearrangement
Yield (chemistry)
Chain walking
remote functionalization
alkenyl cyclopropane
Subjects
Details
- ISSN :
- 21555435
- Database :
- OpenAIRE
- Journal :
- ACS Catalysis
- Accession number :
- edsair.doi.dedup.....386c77fe0075f88ebeebd48d9f13a2f6
- Full Text :
- https://doi.org/10.1021/acscatal.9b00118