Organocatalyst for the Prompt Oxidation of Alcohols
2-Iodo-N-isopropyl-5-methoxybenzamide [I1117] is one of the iodobenzoic acid derivatives used as a catalyst in the oxidation of alcohols. Alcohols are rapidly oxidized in the presence of catalytic amount of I1117, potassium peroxymonosulfate as a cooxidant and tetrabutylammonium hydrogen sulfate as an additive. Secondary and primary alcohols are oxidized to ketones and carboxylic acids, respectively. Not only can I1117 be used as a catalyst in the conversion of tetrahydrofuran-2-methanol derivatives into γ-butyrolactone derivatives but it can also be recovered by purification after the reaction.
Silanol Salt for Deprotection and Cross-coupling Reactions
Potassium trimethylsiloxide [P2356] is used not only in the dealkylation of esters but also as a base in Suzuki-Miyaura cross-couplings, in the disconnection of carbon-silicon bond and hydrolysis of nitriles. It is believed that the dealkylation of esters using P2356 mainly proceeds through a nucleophilic attack of the silanolate anion and can be performed under milder conditions when compared to other reagents with the same reaction mechanism. In the Suzuki-Miyaura cross-coupling, the reaction can proceed rapidly under anhydrous conditions.
Most bioactive substances are optically active. For instance, if a substance is synthesized as a racemic compound, its enantiomer may show no activity or even undesired bioactivity. Thus, methods to synthesize enantiopure compounds have been developed. When synthesizing enantiopure compounds, the methods are roughly divided into three methods: chiral pool method, asymmetric synthesis and optical resolution. TCI offers many chiral auxiliaries for asymmetric synthesis, and chiral resolving reagents as well.
(Triphenylphosphoranylidene)acetonitrile [T1958] is a stable phosphonium ylide, which reacts as a Wittig reagent with a variety of carbonyl compounds to yield α,β-unsaturated nitriles. T1958 can also react with carboxylic acids, in the presence of EDCI and DMAP, to form cyanoketophosphoranes. Ozonolysis of cyanoketophosphoranes, and subsequent addition of nucleophiles such as amines or alcohols, results in α-keto amides, α-keto esters, etc.