Vittorio Montanari

Oxyfunctionalization reactions by perfluoro cis-2,3-dialkyloxaziridines : enantioselective conversion of silanes into silanols

Perfluoro cis-2,3-dialkyloxaziridine 2 is shown to perform the oxyfunctionalization of silanes 1 under very mild conditions to give silanols and silanediols 3 in high chemical yields and complete enantioselectivity.

1-Iodo-polyfluoroalkanes from polyfluoroalkoxy trimethylsilanes and iodochloro triphenylphosphorane

Abstract Polyfluoroalkoxy trimethylsilanes R f CH 2 OSi(CH 3 ) 3 (from the alcohols R f CH 2 OH and HMDS), react with Ph 3 PICl (from ICl and Ph 3 P) eliminating (CH 3 ) 3 SiCl. Pyrolysis of the residues gives Ph 3 PO and pure iodides R f CH 2 I.

A stereoselective and preparative entry to 1,2-anhydrosugars through oxidation of glycals with perfluoro-cis-2,3-dialkyloxaziridines

Perfluoro-cis-2,3-dialkyloxaziridines 1 perform the direct epoxidation of glycals 2 to give cleanly corresponding 1,2-anhydrosugars 3 with medium to complete diastereoselection; elaboration of these glycals to glycosyl fluorides and lipid conjugates is also reported.

Oxidative properties of fluorinated oxaziridines

Abstract Oxaziridines are commonly employed for the epoxidation of olefins, for the oxidation of organometallic species and organo-sulfur, -selenium, -nitrogen compounds, but they have not been used in the oxidation of alcohols. We will describe how perfluorinated oxaziridines can be used for the clean and high yield transformation of secondary alcohols into corresponding ketones. It has been found that perfluoro 2-n-butyl-3-n-propyloxaziridine 1 (prepared in two steps from perfluoro tributylamine) afforded acetone 2 in nearly quantitative yield when reacted with 2-propanol. Similar clean reactions have been observed for more complex substrates such as ethyl lactate, fenchyl alcohol, and androsterone which afforded ethyl pyruvate 3 , fenchone 4 , and androstanedione 5 , respectively. The generality of the process will be presented and reaction conditions employed will be discussed in detail.