METAL-MEDIATED ONE-POT SYNTHESIS OF CYCLOPENTANONES FROM ALLYL VINYL ETHERS OR DIALLYL ETHERS VIA TANDEM CLAISEN REARRANGEMENT AND HYDROACYLATION

Authors
EILBRACHT P GERSMEIER A LENNARTZ D HUBER T
Citation
P. Eilbracht et al., METAL-MEDIATED ONE-POT SYNTHESIS OF CYCLOPENTANONES FROM ALLYL VINYL ETHERS OR DIALLYL ETHERS VIA TANDEM CLAISEN REARRANGEMENT AND HYDROACYLATION, Synthesis, (3), 1995, pp. 330-334
Citations number
53
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
3
Year of publication
1995
Pages
330 - 334
Database
ISI
SICI code
0039-7881(1995):3<330:MOSOCF>2.0.ZU;2-X
Abstract
Cyclopentanones 3 and 7 are generated in a one-pot procedure from ally l vinyl ethers 1 and diallyl ethers 4, respectively. The conversion is carried out in the presence of RhCl(cod)(dppe) or RuCl2(PPh(3))(3) at elevated temperatures and involves a sequence of aliphatic Claisen re arrangement and intramolecular hydroacylation of the pent-4-enals gene rated as intermediates. The diallyl ethers 4 undergo an additional dou ble-bond isomerization prior to the Claisen rearrangement.