1226896-63-4Relevant academic research and scientific papers
Hypervalent Iodine(III)-Catalysed Enantioselective α-Acetoxylation of Ketones
Hokamp, Tobias,Wirth, Thomas
supporting information, p. 10417 - 10421 (2020/07/24)
An enantioselective catalytic synthesis of α-acetoxylated ketones through I(I)/I(III) catalysis using a resorcinol/lactamide-based chiral iodoarene is reported. Catalyst turnover by in situ generation of the active iodine(III) derivative is achieved by oxidation with mCPBA in the presence of acetic acid. The prior transformation of ketones to easily accessible acetyl enol ethers is beneficial and yields up to 97 percent with enantioselectivities up to 88 percent ee are obtained using only low catalyst loadings of only 5 mol percent under mild reaction conditions.
Electron-Deficient Chiral Lactic Acid-Based Hypervalent Iodine Reagents
Qurban, Jihan,Elsherbini, Mohamed,Wirth, Thomas
, p. 11872 - 11876 (2017/11/24)
Novel electron-deficient chiral hypervalent iodine reagents were prepared in good overall yields. The reactivity and stereoselectivity of these reagents in oxidative rearrangements of alkenes to α-aryl ketones were investigated. The results show that the new reagents have good reactivity and generate products with high enantiomeric excess.
Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents
Malmedy, Florence,Wirth, Thomas
supporting information, p. 16072 - 16077 (2016/10/30)
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.
Diastereoselective aminooxygenation and diamination of alkenes with amidines by hypervalent Iodine(III) reagents
Chen, Hui,Kaga, Atsushi,Chiba, Shunsuke
supporting information, p. 6136 - 6139 (2015/01/09)
Diastereoselective anti-aminooxygenation and anti-diamination of alkenes with amidines were enabled by hypervalent iodine(III) reagents such as PhI(OCOR)2 and PhI(NMs2)2, respectively. The present transformation offers diastereochemically pure dihydroimidazoles divergently from E- and Z-alkenes.
Highly stereoselective metal-free oxyaminations using chiral hypervalent iodine reagents
Farid, Umar,Wirth, Thomas
supporting information; experimental part, p. 3462 - 3465 (2012/06/01)
The ring and I: Hypervalent iodine compounds avoid the issues of toxicity or complicated ligands of many transition-metal-based systems. A highly enantioselective oxyamination of alkenes with N-sulfonyl ureas employing chiral, lactic acid-based hypervalent iodine reagents gives a facile synthesis of enantiomerically pure 2-arylproline derivatives (see scheme) for the first time. Copyright
Enantioselective kita oxidative spirolactonization catalyzed by in situ generated chiral hypervalent iodine (iii) species
Uyanik, Muhammet,Yasui, Takeshi,Ishihara, Kazuaki
supporting information; experimental part, p. 2175 - 2177 (2010/06/19)
"Chemical Equation Presented" The iodines(lll) have it: The rational design of a conformationals/ flexible C2symmetric iodosylarene catalyst has been used for the enantioselective Kita oxidative spirolactonization. The reaction occurs through secondary n-σ* or hydrogen-bonding interactions between the chiral catalyst and the substrate. Mes = mesityl (2,4,6-trimethylphenyl).
Chiral hypervalent iodine-catalyzed enantioselective oxidative Kita spirolactonization of 1-naphthol derivatives and one-pot diastereo-selective oxidation to epoxyspirolactones
Uyanik, Muhammet,Yasui, Takeshi,Ishihara, Kazuaki
experimental part, p. 5841 - 5851 (2010/09/08)
We demonstrate here the rational design of a conformationally flexible C2-symmetric iodosylarene 8g based on secondary n-σ or hydrogen-bonding interactions as a chiral catalyst for the enantioselective Kita oxidative spirolactonization of 1-nap
