Selectivity in the Oxidation of Limonene by Amphiphilized Metalloporphyrins in Micellar Media

Abstract

The weak interactions responsible for the aggregation and organization of micellar aggregates have been shown to control the regioselectivity of the epoxidation of limonene catalyzed by manganese porphyrins toward the endo double bond. The same reaction carried out in the presence of aggregates formed by sodium N-dodecanoyl-L-prolinate has shown the same regioselectivity, a selectivity toward the R enantiomer of limonene and a slight but significative stereoselectivity due to the organization of the molecular aggregates.

Manganese(II)-Induced Oxidation of Limonene by Dioxygen

“…Mn(III) porphynins both polymer-supported and in homogeneous system, activate HOOH, PhIO 4 , and NaOCl for selective limonene epoxidation [3][4][5][6][7][8][9][10]. Dioxygen in the presence of an aldehyde (benzaldehyde or pivalaldehyde) was also applied as an oxidant [11][12][13][14].…”

Iron(II, III)-Catalyzed Oxidation of Limonene by Dioxygen

“…Relatively much attention is paid to epoxidation of limonene because the products are valuable starting materials for the synthesis of fragrances and drugs [4]. The epoxidation reactions are performed using mainly heterogeneous catalysts and hydrogen peroxide as an oxidant [5][6][7][8][9][10][11][12]; however, the use of a homogeneous catalyst was also reported [13]. Dioxygen [14][15][16][17] and tert-butyl hydroperoxide [18][19][20][21] were used as oxidants in epoxidation of limonene as well.…”

Spectroscopic, Morphological, and Mechanistic Investigation of the Solvent‐Promoted Aggregation of Porphyrins Modified in meso‐Positions by Glucosylated Steroids

“…The results presented should be of importance for the construction of sensor devices featuring stereoselective features,43 or for obtaining solid‐state materials with chiral properties,44 toward asymmetric catalysis 45. 15d Studies devoted to exploiting the electrochemical behaviour of these interesting systems are underway.…”