Francesco Bonadies

Lanthanides in organic synthesis: Eu+3-catalyzed Michael addition of 1,3- dicarbonyl compounds

EuCl3 proves to be an efficient catalyst for Michael addition of 1,3-dicarbonyl compounds. The employment of Eu+3 chiral complex [Eu(tfc)3] allows the formation of Michael adducts in enantioselective way.

A convenient approach to furan derivatives by I2-induced cyclisation of 2-alkenyl substituted 1,3-dicarbonyl compounds

Abstract 5-iodoalkyl-4,5-dihydrofurans 2 , 5-alkylidine-4,5-dihydrofurans 3 and 2,3,5-trisubstituted furans 4 are obtained through a simple sequence, involving, in the key-step, a regio- and stereoselective iodoenoletherification of 2-alkenyl substituted 1,3-dicarbonyl compounds 1 .

A convenient acid-catalyzed oxidation of sulfides to sulfoxides by t-butyl hydroperoxide

Abstract a very efficient synthesis of sulfoxides is achieved by oxidation of sulfides with t -butyl hydroperoxide catalyzed by camphorsulfonic acid.

A new procedure for Horner-Wadsworth-Emmons olefination of carbonyl compounds

Abstract aldehydes undergo an efficient E-stereoselective Horner-Wadsworth-Emmons olefination by generation of phosphonate carbanion with lithium hydroxide. The reaction proceeds satisfactorily with linear, cyclic, polifunctional ketones in the presence of activated zeolites and and by the slow addition of the base.

Kinetic resolution and asymmetric oxidation as combined routes to chiral sulfoxides

Abstract Non-racemic sulfoxides are accessible through a modified Sharpless kinetic resolution of racemic sulfoxides. Furthermore, thanks to enantioconvergence of asymmetric oxidation and kinetic resolution a successful improvement of e.e. is achievable.

A study on the chelation control in the regioselective opening of 2,3-bifunctionalized epoxides

Abstract The results obtained in the MgBr 2 -mediated opening of 2,3-bifunctionalized epoxides are reported. The studies showed that the chelation control of MgBr 2 between different functionalities can in some cases be selective.

Microwave-assisted oxidation of saturated and unsaturated alcohols with t-butyl hydroperoxide and zeolites

Abstract Under microwave irradiation 3A molecular sieves promote the oxidation of secondary (linear and cyclic) and benzylic alcohols to the corresponding carbonyl compounds by t-butyl hydroperoxide. Under the same conditions, α,β-unsaturated alcohols are converted into α,β-epoxyalcohols in regio- and diastereoselective way. Both oxidative processes can be performed under solvent-free conditions; however, epoxidation of allylic alcohols is found to proceed with more satisfactory efficiency in saturated aliphatic hydrocarbon (n-hexane or cyclohexane).

Studies on asymmetric synthesis of β-hydroxy-δ-lactone inhibitors of HMGCoA reductase 1. A new preparation of the lactone moiety of compactin

Abstract a new strategy for the preparation of chiral β-hydroxy-δ-lactone inhibitors of HMGCoA reductase is outlined: in particular the compactin lactone moiety has been elaborated by asymmetric epoxidation of the appropriate allylic alcohol and subsequent introduction of the second chiral center via a new Ti(OiPr)4 mediated reduction of β-hydroxy ketones.

Reactivity of furylhydroperoxides in asymmetric oxidation and kinetic resolution

Abstract Furylhydroperoxides can be successfully employed in the enantioselective oxidation of allylic alcohols and sulfides under Sharpless-type conditions. Their kinetic resolution provides a mean both to chiral furylhydroperoxides and furylalcohols.

Diastereoselective epoxidation of allylic alcohols by t-butyl hydroperoxide/zeolites system

Abstract Commercial zeolites promotes the epoxidation of unsaturated alcohols in chemo- and diastereoselective way.