594822-19-2Relevant articles and documents
Synthesis of conjugated γ- and δ-lactones from aldehydes and ketones via a vinylation(allylation)-ring closing metathesis-oxidation sequence
Marco, J. Alberto,Carda, Miguel,Rodríguez, Santiago,Castillo, Encarnación,Kneeteman, María N.
, p. 4085 - 4101 (2007/10/03)
Nucleophilic C-vinylation and C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl or homoallyl ethers, respectively. Ring-closing metathesis of these compounds afforded in many cases cyclic ethers (dihydrofurans and dihydropyrans, respectively) bearing disubstituted and trisubstituted C=C bonds. These were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones. Reasons for the observed failures are presented and discussed.