49 research outputs found
Enantioselective oxidative rearrangements with chiral hypervalent iodine reagents
A stereoselective hypervalent iodine-promoted oxidative rearrangement of 1,1-disubstituted alkenes has been developed. This practically simple protocol provides access to enantioenriched α-arylated ketones without the use of transition metals from readily accessible alkenes
Stereoselective ketone rearrangements with hypervalent iodine reagents
The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved
Oxidative Rearrangements of Arylalkanones with 1H-1-Hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-Dioxide, a “Green” Analogue of Koser′s Reagent.
ChemInform Abstract: Stereoselective Synthesis and X-Ray Structures of Alkenyliodonium Salts with a Pyridine N-Oxide Moiety.
Oxidative Rearrangements of Arylalkenes with [Hydroxy(tosyloxy)iodo]benzene in 95% Methanol: A General, Regiospecific Synthesis of α-Aryl Ketones.
Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β-Benzocyclo-alkenones from α-Benzocycloalkenones
The conversion of α-benzocycloalkenones to homologous β-benzocyclo-alkenones containing six, seven and eight-membered rings is reported. This wasaccomplished via a Wittig olefination-oxidative rearrangement sequence using[hydroxy(tosyloxy)iodo]-benzene (HTIB) is the oxidant, that enables the synthesis ofregioisomeric pairs of methyl-substituted β-benzocycloalkenones. The incorporation ofcarbon-13 at C-1 of the β-tetralone nucleus was also demonstrated. The Wittig-HTIBapproach is a useful alternative to analogous sequences in which Tl(NO3)3·3H2O or thePrevost combination (AgNO3/I2) are employed in the oxidation step