923570-05-2Relevant academic research and scientific papers
N-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesizecis-enamides through vinyl benziodoxolones
Shimbo, Daisuke,Maruyama, Toshifumi,Tada, Norihiro,Itoh, Akichika
supporting information, p. 2442 - 2447 (2021/04/02)
The stereoselective synthesis ofcis-β-N-alkoxyamidevinyl benziodoxolones (cis-β-N-RO-amide-VBXs) fromO-alkyl hydroxamic acids in the presence of an ethynyl benziodoxolone-acetonitrile complex (EBX-MeCN) is reported herein. The reaction was performed under mild conditions including an aqueous solvent, a mild base, and room temperature. The reaction tolerated variousO-alkyl hydroxamic acids derived from carboxylic acids, such as amino acids, pharmaceuticals, and natural products. Vinyl dideuteratedcis-β-N-MeO-amide-VBXs were also synthesized using deuterium oxide as the deuterium source. Valine-derivedcis-β-N-MeO-amide-VBX was stereospecifically derivatized to hydroxamic acid-derivedcis-enamides without the loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.
Ligand-Accelerated Palladium(II)-Catalyzed Enantioselective Amination of C(sp2)-H Bonds
Cheng, Xiu-Fen,Fei, Fan,Li, Yan,Hou, Yi-Ming,Zhou, Xin,Wang, Xi-Sheng
supporting information, p. 6394 - 6398 (2020/08/24)
The first example of the Pd(II)-catalyzed enantioselective amination of aryl C-H bonds is reported. The key to the successful realization of this asymmetric catalytic transformation was the identification of mono-N-protected α-amino-O-methylhydroxamic acid (MPAHA) ligands, which promote reactivity under mild conditions and control enantioselectivity. The counteranions in the solvent medium, hexafluoroacetylacetate and acetate, were also found to play key roles in stereocontrol and reactivity enhancement.
Bifunctional amino sulfonohydrazide catalyzed direct asymmetric mannich reaction of cyclic ketimines with ketones: Highly diastereo-and enantioselective construction of quaternary carbon stereocenters
Zhang, Sheng,Li, Lijun,Hu, Yanbin,Zha, Zhenggen,Wang, Zhiyong,Loh, Teck-Peng
supporting information, p. 1050 - 1053 (2015/03/30)
A bifunctional amino sulfonohydrazide which contains multiple sites for hydrogen bonding with substrates was found to enhance reactivity and enantioselectivity in the direct asymmetric Mannich reaction of N-sulfonyl cyclic ketimines with ketones. In this efficient transformation, not only methyl ketones but also cyclic ketones can be employed to provide a general methodology to construct tetrasubstituted α-amino ester in a stereoselective manner. The synthetic utility of a substituted amino ester product is demonstrated by the synthesis of biologically active spirotetrahydrofuran.
Development of potent, orally active 1-substituted-3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors
Birch, Alan M.,Kenny, Peter W.,Oikonomakos, Nikos G.,Otterbein, Ludovic,Schofield, Paul,Whittamore, Paul R.O.,Whalley, Dave P.
, p. 394 - 399 (2007/10/03)
A series of substituted 3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors, which have potential as antidiabetic agents, is described. Initial members of the series showed good enzyme inhibitory potency but poor physical properties. Optimisation of the 1-substituent led to 2,3-dihydroxypropyl compounds which showed good in vitro potency and improved physical properties, together with good DMPK profiles and acute in vivo efficacy in a rat model. X-ray crystallographic data are presented, showing an unexpected variety of binding orientations at the dimer interface site.
