Tuning the Chemoselectivity of Silyl Protected Rhamnals by Temperature and Brønsted Acidity: Kinetically Controlled 1,2-Addition vs Thermodynamically Controlled Ferrier Rearrangement.
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DOI: 10.1021/acs.orglett.9b00009
Abstract: An acidity- and temperature-dependent chemoselective glycosylation of silyl-protected rhamnals with alcohols has been revealed. The reaction undergoes a 1,2-addition pathway with (±)-CSA as the catalyst at rt, affording kinetically controlled 2-deoxyl rhamnosides. In contrast, only… read more here.
Keywords: ferrier rearrangement; temperature; silyl protected; thermodynamically controlled ... See more keywords
Stereomutation and chiroptical bias in the kinetically controlled supramolecular polymerization of cyano-luminogens
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DOI: 10.1039/d2sc03449b
Abstract: The synthesis of two pairs of enantiomeric cyano-luminogens 1 and 2, in which the central chromophore is a p-phenylene or a 2,5-dithienylbenzene moiety, respectively, is described and their supramolecular polymerization under kinetic and thermodynamic control… read more here.
Keywords: aggregation; cyano luminogens; supramolecular polymerization; thermodynamically controlled ... See more keywords