Posts by Category: Reactions

Shenvi Isonitrile Synthesis

Shenvi Isonitrile Synthesis

General Characteristics Shenvi reported recently that isonitriles can be prepared by substitution of tertiary alcohols using TMSCN with the inversion of stereochemistry. Isonitriles can be regarded ...

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Bohlmann-Rahtz Pyridine Synthesis

Bohlmann-Rahtz Pyridine Synthesis

General Characteristics Pyridines can be synthesized by condensation of appropriately substituted enamines and ethynyl ketones, which proceeds via aminodiene intermediates. General References ...

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Hauser-Kraus Annulation

Hauser-Kraus Annulation

General Characteristics The synthesis of naphthalene hydroquinones from phthalide anions and α,β–undaturated carbonyl compounds through the Michael addition-then-Dieckmann condensation is known as ...

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Davis Oxidation

Davis Oxidation

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 ...

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MSH Reagent

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 ...

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Hartwig-Miyaura C-H Borylation

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 ...

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Marshall Propargylation

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 ...

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Rubottom Oxidation

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 ...

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Oxidation with Dioxiranes

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 ...

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Shi Asymmetric Epoxidation

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 ...

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