General Characteristics -Alkenes can be converted into anti-Markovnikov alcohols by the Brown hydroboration, which involves regio/stereoselective syn-addition of a B-H bond to the olefin followed by ...
Posts by Category: Reactions
Carbamate Protective Groups
General Characteristics In order to tame the basicity and the high reactivity of amines during multi-step synthesis, it is common to protect them with electron-withdrawing functional groups. ...
Acetal Protective Groups
General Characteristics Alcohols can be protected as acetals against reductive and basic conditions. Oxygen-based acetals are also stable under oxidizing conditions. Deprotection is usually done ...
Olefin Metathesis
General Characteristics In the presence of a metal alkylidene catalyst, two olefins combine and redistribute their fragments to give a new pair of olefins. Olefin metathesis is fundamentally an ...
Ether Protective Groups
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), ...
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 ...