Back to Search
Start Over
Ruthenium-catalyzed cyclizations of enynes via a ruthenacyclopentene intermediate: development of three novel cyclizations controlled by a substituent on alkyne of enyne.
- Source :
-
Chemical record (New York, N.Y.) [Chem Rec] 2011 Aug; Vol. 11 (4), pp. 186-98. Date of Electronic Publication: 2011 Aug 09. - Publication Year :
- 2011
-
Abstract
- Three novel ruthenium-catalyzed cyclizations of enynes were developed. In each cyclization, a ruthenacyclopentene derived from enyne and Cp*RuCl(cod) is a common intermediate. When an enyne having an alkyl, an ester, or a formyl group on an alkyne was reacted with Cp*RuCl(cod) under ethylene gas, ethylene was inserted into the ruthenium-sp(2) carbon bond of ruthenacyclopentene to afford ruthenacycloheptene, and β-hydrogen elimination followed by reductive elimination occurred to give a cyclic compound having a 1,3-diene moiety. When an acyl group was placed on the alkyne, the carbonyl oxygen coordinated to the ruthenium metal of ruthenacyclopentene to produce a ruthenium carbene complex, which reacted with ethylene to give a cyclic compound having a cyclopropane ring on the substituent. On the other hand, when the substituent on the alkyne was pent-4-enyl, insertion of an alkene part into ruthenacyclopentene followed by reductive elimination gave a tricyclic compound by a ruthenium-catalyzed [2+2+2] cyclization of diene and an alkyne.<br /> (Copyright © 2011 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.)
Details
- Language :
- English
- ISSN :
- 1528-0691
- Volume :
- 11
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- Chemical record (New York, N.Y.)
- Publication Type :
- Academic Journal
- Accession number :
- 21830297
- Full Text :
- https://doi.org/10.1002/tcr.201100003