135218-50-7Relevant academic research and scientific papers
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.
New [Ru3(CO)12]-Based Catalysts with Imidazolinium Salt, Diimine, or Bis(oxazoline) Ligands and Ruthenium Bis(oxazoline) Complex for Tandem Isomerisation/Claisen Rearrangement of Dienyl Ethers - X-ray Structure of [RuCl{(R,R)-bis(iso
Ammar, Hamed Ben,Le Notre, Jerome,Salem, Mansour,Kaddachi, Mohamed T.,Toupet, Loic,Renaud, Jean-Luc,Bruneau, Christian,Dixneuf, Pierre H.
, p. 4055 - 4064 (2007/10/03)
The reaction of various 1,7-dienes in the presence of the three-component catalyst A: [Ru3(CO)12]/imidazolinium salt/Cs 2CO3 (1:1:2) leads to the tandem alkene isomerisation/ Claisen rearrangement affording γ,δ-
A synthesis of densely functionalized 2,3-dihydropyrans using ring-closing metathesis and base-induced rearrangements of dihydropyran oxides
Schmidt, Bernd,Wildemann, Holger
, p. 3145 - 3163 (2007/10/03)
The preparation of dihydropyran and dihydrofuran oxides and their rearrangement in the presence of lithium dialkylamides to functionalized 2,3-dihydropyrans or 2,3-dihydrofurans, respectively, is described. The regiochemical outcome of the reaction can be influenced by the relative configuration of the starting epoxides and the steric demand of the base. The 2,3-dihydropyrans obtained were converted stereoselectively to difunctionalized 3,4-dihydropyrans by the carbon-Ferrier reaction, or to fused acetals by addition of dimedone, mediated by ceric ammonium nitrate. The stereochemical results are rationalized by mechanistic proposals.
Synthesis of conjugated γ- and δ-lactones from aldehydes and ketones via a vinylation/allylation-ring closing metathesis-oxidation sequence
Carda, Miguel,Castillo, Encarnación,Rodríguez, Santiago,Uriel, Santiago,Marco, J. Alberto
, p. 1639 - 1641 (2007/10/03)
Nucleophilic C-vinylation or C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl ethers. Ring-closing metathesis of the latter afforded cyclic ethers (dihydrofurans and dihydropyrans, respectively) which were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones.
