80751-97-9Relevant academic research and scientific papers
Transition metal complexes of new glyoxylato-aroylhydrazones and their role in l-ascorbic acid oxidation inhibition
Csonka, Robert,Villalonga-Barber, Carolina,Psycharis, Vassilis,Raptopoulou, Catherine P.,Steele, Barry R.
, p. 181 - 187 (2012)
We report here the synthesis of new ligands of the aroylhydrazone family. Glyoxylato-aroylhydrazones (gly-AH) with lipophilic character were designed for possible biological applications where metal chelation is desired. They were found to coordinate read
Improved Synthesis of MediPhos Ligands and Their Use in the Pd-Catalyzed Enantioselective N-Allylation of Glycine Esters
Albat, Dominik,Neud?rfl, J?rg-Martin,Reiher, Martin,Schmalz, Hans-Günther
, p. 4237 - 4242 (2021/08/24)
A new class of chiral C2-symmetric diphosphines (MediPhos) was recently shown to give superior results in the Pd-catalyzed asymmetric N-allylation of amino acid esters. We here describe a new, improved protocol for the preparation of such ligands through bidirectional SN2-coupling of a tartrate-derived ditosylate with 6-alkyl-2-bromophenols followed by double lithiation/phosphanylation. This method gave access to a series of nine ligands with branched alkyl substituents, which were benchmarked in the enantioselective Pd-catalyzed N-allylation of tert-butyl glycinate with racemic (E)-2,8-dimethylnona-5-en-4-yl methyl carbonate (up to 95 % ee). In addition, the analogous transformation of tert-butyl glycinate with methyl (E)-nona-5-en-4-yl carbonate was optimized. The obtained allylic amines were then used in the stereoselective synthesis of the conformationally restricted proline-derived dipeptide analogs ProM-17 and ProM-21.
Selective catalytic carbanionic ethylation of methylphenols: Influence of catalyst and substitution pattern
Steele, Barry R.,Villalonga-Barber, Carolina,Micha-Screttas, Maria,Screttas, Constantinos G.
, p. 2093 - 2097 (2007/10/03)
Addition of ethylene to the carbanions formed by the metallation of the lithium salts of di- and trimethylphenols by the strongly basic system, n-BuLi-LiK(OCH2CH2NMe2)2 provides a useful synthetic route to a range of alkylphenols. The ease of alkylation of the methyl groups decreases in the order ortho>meta>para while the inclusion of Mg(OCH2CH2OEt)2 in the catalyst restricts alkylation to the methyl groups ortho to the hydroxy group. Dialkylation occurs only at the ortho-methyl groups and only if the adjacent meta-position is unsubstituted. The potential of these products for the synthesis of sterically hindered ligands is outlined.
Nucleophilic Displacement with Heterocycles as Leaving Groups. Part 16. Reactions of Secondary Alkyl Primary Amines with 5,6,8,9-Tetrahydro-7-phenyldibenzoxanthylium Trifluoromethanesulphonate to give Intermediates Solvolysing without Rearrangement
Katritzky, Alan R.,Lopez-Rodriguez, Maria L.,Keay, James G.,King, Roy W.
, p. 165 - 170 (2007/10/02)
Representative secondary alkyl primary amines R1R2CHNH2 react with the title pyrylium cation in acetic acid, alcohols, phenols, and NN-dimethylaniline acting as nucleophilic solvents to give O- and C-(secondary alkyl) products.Absence of carbenium ion rearrangements is consistent with reaction via intimate ion-molecule pairs formed rapidly from the corresponding pyridinium cations.
