Oxidation Of Homoallylic Alcohols Research Articles

ChemInform Abstract: Catalyst‐Controlled Wacker‐Type Oxidation of Homoallylic Alcohols in the Absence of Protecting Groups.

AbstractIn the presence of tBuOOH and the catalyst system, various homoallylic alcohols undergo selective oxidation to β‐hydroxyketones.

Thallium(III) in Organic Synthesis

This review article discusses the literature regarding thallium(III)compounds in synthetic organic chemistry published in the last decade,including several applications in the total synthesis of naturalproducts. The reactions that received the most attention in thisperiod were: i) the oxidative rearrangement of chalcones; ii) thering contraction of cyclic alkenes; iii) the oxidation of homoallylicalcohols; iv) aromatic thallations; and v) oxidative couplings,including with phenols. 1 Introduction 2 Non-Oxidative Reactions 3 Oxidative Reactions 3.1 Oxidations with Rearrangement 3.1.1 Ketones 3.1.1.1 Alkyl Aryl Ketones 3.1.1.2 Cyclic Ketones 3.1.1.3 Flavanones 3.1.1.4 Chalcones 3.1.2 Alkenes 3.1.3 Ring Opening of Cyclopropanes 3.2 Oxidations without Rearrangement 3.2.1 Cyclization Reactions 3.2.1.1 Alkenols 3.2.1.2 Carboxylic Acids 3.2.2 α-Oxidation of Ketones 3.2.3 Aromatic Thallation 3.2.4 Oxidative Coupling 3.2.4.1 Phenolic Oxidative Coupling 3.2.4.2 Non-Phenolic Oxidative Coupling 3.2.5 Oxidation of Phenols 3.2.6 Oxidation of Nitrogen Compounds 3.2.7 Disulfide Bond Formation 3.2.8 Deprotection of Thioketals 4 Miscellaneous 5 Conclusions

Further studies of an approach to a total synthesis of phomactins

The bicyclic sulfone 28, which has the intact carbon skeleton of phomactins, was prepared using a stereoselective [2,3]-Wittig Still rearrangement, a ytterbium triflate-mediated addition of a vinyllithium reagent to an aldehyde and macrocyclisation via an intramolecular sulfone alkylation, as key steps. During studies into the conversion of this intermediate into phomactin A, it was found that oxidation of homoallylic alcohols using TPAP can give unsaturated keto-aldehydes, and the stereoselectivity of reduction of a ketone at C(14) is influenced by the presence of a remote sulfonyl group at C(10).

Pb(OAc) 4 mediated transannular oxidative ring cleavage

Pb(OAc) 4 oxidation of homoallylic alcohols at room temperature leads to the formation of a variety of fragmentation products, whose formation requires spatial proximity of the alcohol and the olefin moieties.

A novel oxidation of homoallylic alcohols under sonochemical conditions

The oxidation of 3β-hydroxy-Δ5-cholestenes, -pregnenes and -androstenes to the corresponding Δ4-3,6-diones has been achieved in high yields by a new one-step process, using tetra-n-propylammonium perruthenate with 4-methylmorpholine N-oxide as co-oxidant, under sonochemical conditions.