The title compound, C30H28O2, was obtained during recrystallization of (±)-1,2-diphenyl-1,2-propane-diol in 1-butanol, from an unexpected non-acid-catalyzed pinacol rearrangement followed by acetal formation of the newly formed aldehyde with the diol. The tri-substituted dioxolane ring has a twist conformation on the C-O bond opposite the methyl-substituted C atom. There is an intra-molecular C...

The use of tethers allows to overcome reactivity and selectivity issues often encountered with intermolecular reactions. Although tethers have been successfully applied for decades, their installation and removal usually requires additional steps. This minireview highlights the recent development of tethers that can be installed in situ on (homo)-allyl amines or alcohols for Tsuji-Trost allylat...

A series of cyclic acetals were investigated with regard to their ability to function as coinitiators in free-radical photopolymerization induced by camphorquinone (CQ). Among these cyclic acetals, the reactivity of 2-hexyl-1,3-benzodioxole (HBDO) was the highest, according to the quantum yield of CQ. However, the most efficient coinitiator was l,3-benzodioxolane, which has a reactivity signifi...

Asymmetric synthesis of drug-like functionalized spiro[chroman-3,3'-indolin]-2'-ones 5 containing three contiguous stereocenters with high diastereo- and enantioselectivities was achieved using the reflexive-Michael (r-M) reaction of unmodified hydroxyenals 1 with various (E)-3-alkylideneindolin-2-ones 2 in the presence of (R)-DPPOTMS/AcOH (R)-3/4b as a catalyst at room temperature. Chiral spir...

The regioselective C-2-O-acrylation and metacrylation of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and methyl 4,6-O-benzylidene-alpha-D-galactopyranoside through their corresponding organotin intermediates have been studied. Regioselectivity was achieved through the formation of a tin chelate of the 2,3-diols. Thus, methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and methyl 4,6-O-benzyl...

Alkaline anodic oxidation of glycerol suffers from facile C−C bond cleavage, especially when using non-precious metal electrocatalysts, which limits the yield more valuable C3 oxygenates. Usually, a high selectivity is tradeoff with conversion for most catalysts. Thus, we used solketal as reactant, acetal-protected acetone. CV experiments showed that oxidized over nickel boride (NixB) at potent...

In the course of a study of the analytical determination of ester groupings in naturally occurring phospholipides, we found that a specimen of beef heart lecithin, prepared according to the method of Pangborn (l), regularly gave ester values considerably below those obtained with egg lecithin. The preparation was presumably pure, since it was colorless, free of amino nitrogen, had a molar N:P r...