4861-78-3Relevant academic research and scientific papers
Neighboring Group Participation in Lewis Acid-Promoted and Annulations. The Stereocontrolled Synthesis of Tricyclic Ethers
Molander, Gary A.,Cameron, Kimberly O.
, p. 5931 - 5943 (2007/10/02)
A variety of 1,4- and 1,5-keto aldehydes derived from cycloalkanes are coupled with the bis(trimethylsilyl) enol ether of methyl acetoacetate in the presence of either TMSOTf or TrSbCl6 to generate tricyclic ethers.The reactions proceed with excellent regiochemical control by a mechanism involving neighboring group participation.This mechanism involves initial formation of a bicyclic oxocarbenium ion intermediate from the keto aldehyde substrates.The geometries of selected bicyclic intermediates have been optimized using the AM1 method allowing successful prediction of the stereochemical outcomes in the cyclization in most cases.Epimerization of α-chiral keto aldehyde substrates does not appear to occur in these Lewis acid-promoted annulation reactions.
INTRAMOLECULAR SULFOR-YLIDE ADDITIONS TO KETONES. A CYCLOPENTANE ANNULATION
Crandall, J. K.,Magaha, H. S.,,Widener, R. K.,Tharp, G. A.
, p. 4807 - 4810 (2007/10/02)
Various 2-(3'-phenylthiopropyl)cycloalkanones were prepared from the corresponding ketones and subjected to S-alkylation by triethyloxonium tetrafluoroborate followed by potassium tert-butoxide treatment to give bicyclic epoxides with new five-membered ca
