General Characteristics Ethers are stable under a wide range of conditions and relatively robust protecting groups. Methyl (Me) and trityl (Tr) groups are commonly used along with benzyl (Bn), ...
Monthly Archives: March 2014
Horner-Wadsworth-Emmons (HWE) Reaction
General Characteristics -The reaction between a phosphonate ylide and an aldehyde, which proceeds via mechanistic path similar to the Wittig reaction to give an α,β-unsaturated ester. -The ...
Diels-Alder Reaction
General Characteristics -The most classic example of [4+2] cycloaddition reaction in which a diene and a dienophile combine to give a cyclohexene. The reaction generally proceeds with good stereo- ...
Negishi Cross Coupling Reaction
General Characteristics -While cross coupling reactions based on organolithium and Grignard reagents (Kumada-Tamao-Corriu cross coupling) tend to suffer from unwanted side reactions when applied to ...
Swern Oxidation
General Characteristics -The oxidation of alcohols based on the dimethylsulfoxide (DMSO)-oxalyl chloride system is called the Swern oxidation. -DCC (Pfitzner-Moffatt), TFAA (modified Swern), acetic ...
Dess-Martin Oxidation
General Characteristics -The oxidation of alcohols by Dess-Martin periodinane (DMP). -The reaction proceeds at room temperature, converting alcohols into aldehydes. -Reactive and mild enough to be ...
Mizoroki-Heck Reaction
General Characteristics -The cross coupling reaction between an aryl/alkenyl halide and a terminal olefin in the presence of a Pd(0) catalyst to produce a substituted olefin is called the ...
Sonogashira-Hagiwara Cross Coupling Reaction
General Characteristics -The cross coupling reaction between an aryl or alkyl halide and a terminal alkyne catalyzed by the combination of Pd(0), copper iodide, and an amine is called the ...
p-Methoxybenzyl (PMB) Protective Group
General Characteristics –p-Methoxybenzyl (PMB or MPM) group can be protected or deprotected under the same conditions as benzyl group. It can also be deprotected under mildly oxidizing ...
Mitsunobu Reaction
General Characteristics -A secondary alcohol reacts with diethyl azodicarboxylate (DEAD), triphenylphosphine (Ph3P), and benzoic acid to give a corresponding benzoyloxy derivative with the inversion ...