General Characteristics Ketones and esters can be hydroxylated at the α-position when their enolates are treated with 2-sulfonyloxaziridine (N-sulfonyloxaziridine, the Davis reagent). Asymmetric ...
Monthly Archives: October 2015
MSH Reagent
General Characteristics MSH (O-(mesitylsulfonyl)hydroxylamine) is an electrophilic aminating agent used to introduce a NH2 unit. It is used in reactions such as the Beckmann rearrangement, the Neber ...
Hartwig-Miyaura C-H Borylation
General Characteristics Iridium catalysts coordinated with electron-donating bidentate ligands promote direct C-H borylation of non-halogenated aromatic rings. Organoboronate compounds are, of ...
Marshall Propargylation
General Characteristics In the Marshall propargylation, propargyl mesylates and aldehydes are reductively coupled to form a new carbon-carbon bond. The transfer of chirality from the mesylates ...
Rubottom Oxidation
General Characteristics The epoxidation of silyl enol ethers with oxidants such as mCPBA and dioxirane leads to rearrangement into α-silyloxyketones. This reaction is used commonly to introduce a ...
Oxidation with Dioxiranes
General Characteristics Dimethyldioxirane (DMDO), prepared from acetone and Oxone®, is used frequently to oxidize alkenes to epoxides. Methyl(trifluoromethyl)dioxirane (TFDO) is about 600 times more ...
Shi Asymmetric Epoxidation
General Characteristics The asymmetric epoxidation of alkenes using the in situ generated chiral dioxirane formed from the fructose-derived ketone pre-catalyst and Oxone® (potassium ...