1007560-45-3Relevant academic research and scientific papers
Rh-catalyzed formation of dioxolanes from α-alkyl diazoesters: Diastereoselective cycloadditions of carbonyl ylides with selectivity over β-hydride elimination
DeAngelis, Andrew,Panne, Patricia,Yap, Glenn P. A.,Fox, Joseph M.
, p. 1435 - 1439 (2008)
(Chemical Equation Presented) Described here is a diastereoselective Rh-catalyzed method for the preparation of dioxolanes from α-alkyl- α-diazoesters. This represents the first general method for generating carbonyl ylides from α-diazoesters that possess β-hydrogens, as such diazo compounds typically give rise to alkenes via β-hydride elimination. Subsequent cycloaddition with aromatic aldehydes gives tetrasubstituted dioxolanes with unusually high diastereoselectivity. A model is set forth to explain the diastereoselectivity of the cycloaddition.
Rh-catalyzed intermolecular cyclopropanation with α-alkyl-α- diazoesters: Catalyst-dependent chemo- and diastereoselectivity
Panne, Patricia,DeAngelis, Andrew,Fox, Joseph M.
body text, p. 2987 - 2989 (2009/04/18)
(Chemical Equation Presented) A Rh-catalyzed procedure for the cyclopropanation of alkenes with α-alkyl-α-diazoesters is described. With dirhodium tetraoctanoate, the predominant pathway is β-hydride elimination. While a number of sterically demanding carboxylate ligands serve to avoid β-hydride elimination, it was found that triphenylacetate (TPA) also imparts high diastereoselectivity.
