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Relevant academic research and scientific papers

A diacetate ketone-catalyzed asymmetric epoxidation of olefins

(Chemical Equation Presented) A fructose-derived diacetate ketone has been shown to be an effective catalyst for asymmetric epoxidation. High ee values have been obtained for a variety of trans and trisubstituted olefins including electron-deficient α,β-unsaturated esters as well as certain cis olefins.

Asymmetric epoxidation catalyzed by α,α-dimethylmorpholinone ketone. Methyl group effect on spiro and planar transition states

(Chemical Equation Presented) Asymmetric epoxidation of olefins by using an α,α-dimethylmorpholinone-containing chiral ketone catalyst (4) has been investigated. This ketone, which has the combined features of several previously studied catalysts, is an effective catalyst for trans- and trisubstituted olefins, and up to 97% ee has been achieved. The R, R-dimethyl group has significant impact on spiro and planar transition states.

Chiral Lewis acid catalyzed resolution of racemic enol ester epoxides. Conversion of both enantiomers of an enol ester epoxide to the same enantiomer of acyloxy ketone

This paper describes an efficient kinetic resolution of racemic enol ester epoxides via a chiral Lewis acid catalyzed rearrangement. Both enantiomerically enriched enol ester epoxides and α-acyloxy ketones can be obtained through this resolution. A positive nonlinear effect is observed in this process. By taking advantage of the mechanistic duality in acid-catalyzed enol ester epoxide rearrangement, we can completely convert a racemic enol ester epoxide into an enantiomerically enriched α-acyloxy ketone by treatment with a catalytic amount of a chiral Lewis acid followed by a catalytic amount of an achiral protic acid.

An efficient ketone-catalyzed asymmetric epoxidation using hydrogen peroxide (H2O2) as primary oxidant

High enantioselectivities have been obtained for asymmetric epoxidation of olefins using a fructose-derived chiral ketone (5) as catalyst and hydrogen peroxide as primary oxidant.

Electronic probing of ketone catalysts for asymmetric epoxidation. Search for more robust catalysts

Equation presented Ketones with a fused oxazolidinone were synthesized and investigated to determine the electronic effect of the substituents at α-positions of ketone catalysts on the Baeyer-Villiger oxidation and catalytic properties for asymmetric epoxidation. These new ketones give high yields and ee's with only 1 5 mol % catalyst. The current studies further show that the electronic effect is very important for the kitone-catalyzed epoxidation.

Enantioselective synthesis and stereoselective rearrangements of enol ester epoxides

Enol esters can be epoxidized with high enantioselectivities using the fructose-derived chiral ketone 1 as catalyst and Oxone as oxidant. A detailed study of enantiomerically enriched enol ester epoxides has revealed that the acid-catalyzed rearrangement can proceed through two distinct pathways, one with retention of configuration and the other with inversion. The competition between the two pathways is highly dependent upon the nature of the acid catalyst. A strong acid favors retention of configuration and a weak acid favors inversion of configuration. Under thermal conditions, these epoxides rearrange highly stereoselectively with inversion of configuration. Either enantiomer of an α-acyloxy ketone can be formed from one enantiomer of an enol ester epoxide by judicious choice of reaction conditions.

Asymmetric epoxidation using hydrogen peroxide (H2O2) as primary oxidant

High enantioselectivities have been obtained for asymmetric epoxidation of olefins using a fructose-derived chiral ketone as catalyst and hydrogen peroxide as primary oxidant.

Highly enantioselective epoxidation of enol silyl ethers and esters

High enantioselectivities have been obtained for asymmetric epoxidation of enol silyl ethers and esters using a fructose-derived chiral ketone as catalyst and Oxone as oxidant.