134829-38-2Relevant academic research and scientific papers
γ-Lactone-tethered ring-closing metathesis. A route to enantiomerically enriched γ-lactones α,β-fused to medium-sized rings
Rodriguez, Carmen M.,Ravelo, Jose Luis,Martin, Victor S.
, p. 4787 - 4789 (2004)
(Chemical Equation Presented) The stereoselective alkylation of α(phenylsulfonyl)-β-[(methoxycarbonyl)methyl]-γ-lactones obtained by the base-induced cyclization of enantiomericaily enriched α-[(phenylthio)acyl]-α,β-unsaturated esters and ring-closing olefin metathesis (RCM) are the basis of a new approach for gaining access to γ-lactones that are α,β-fused to medium-sized carbocycles and cyclic ethers.
γ-Lactones as templates in ring-closing metathesis: Enantioselective synthesis of medium sized carbocycles fused to butyrolactones
Ravelo, José Luis,Rodríguez, Carmen Ma,Martín, Víctor S.
, p. 5326 - 5335 (2007/10/03)
A methodology for accessing enantiomerically enriched carbocyclic systems fused to γ-lactones is described. Key steps are the stereoselective synthesis of highly substituted γ-lactones and ring-closing metathesis of the suitable ramifications. The process permits the choice of stereochemistry, regioselectivity and ring size of the fused compounds.
Stereoselective Synthesis of Highly Substituted γ-Lactones and Butenolides by Intramolecular Michael Addition of Enantiomerically Enriched γ-oxy α,β-Unsaturated Esters
Rodriguez, Carmen M.,Martin, Tomas,Ramirez, Miguel A.,Martin, Victor S.
, p. 4461 - 4472 (2007/10/02)
The synthesis of polysubstituted γ-lactones by the base-induced cyclization of enantiomerically enriched γ-oxy α,β-unsaturated esters obtained from 2,3-epoxy alcohols is described.The procedure is highly stereoselective and compatible with a wide range of functionalities (ester, tetrahydropyranyl ether, silyl ether, etc.).Varying degrees of substitution, including quaternary centers, in the final γ-lactone were synthesized with excellent stereoselectivity.Useful functional interconversions were successfully demonstrated, in particular those resulting in butenolides.By the use of AM1 it was concluded that the intramolecular Michael reaction can be described as a kinetically controlled reaction in which the relative stability of the transition states for all possible final configurations led to geometries in agreement with the experimental results.
An approach to the stereocontrolled synthesis of polysubstituted chiral butenolides and γ-lactones
Rodriguez, Carmen M.,Martin, Victor S.
, p. 2165 - 2168 (2007/10/02)
The enantioselective synthesis of polysubstituted butenolides and γ-lactones by an intramolecular Michael addition of chiral thiophenylacetates of γ-hydroxy-α,β-unsaturated esters is described.
