58379-86-5Relevant articles and documents
Alkenyl Isocyanide Conjugate Additions: A Rapid Route to γ-Carbolines
Chepyshev, Sergiy V.,Lujan-Montelongo, J. Armando,Chao, Allen,Fleming, Fraser F.
, p. 4310 - 4313 (2017/04/04)
Isocyanides are exceptional building blocks, the wide deployment of which in multicomponent and metal-insertion reactions belies their limited availability. The first conjugate addition/alkylation to alkenyl isocyanides is described, which addresses this deficiency. An array of organolithiums, magnesiates, enolates, and metalated nitriles add conjugately to β- and β,β-disubstituted arylsulfonyl alkenyl isocyanides to rapidly assemble diverse isocyanide scaffolds. The intermediate metalated isocyanides are efficiently trapped with electrophiles to generate substituted isocyanides incorporating contiguous tri- and tetra-substituted centers. The substituted isocyanides are ideally functionalized for elaboration into synthetic targets as illustrated by the three-step synthesis of γ-carboline N-methyl ingenine B.
Sulfination of Alcohols with p-Toluenesulfonylmethyl Isocyanide under Metal-Free Conditions: A Mitsunobu Approach
Kadari, Lingaswamy,Radha Krishna, Palakodety,Lakshmi Prapurna
supporting information, p. 3863 - 3868 (2016/12/16)
A Mitsunobu approach for the synthesis of sulfinate esters by direct nucleophilic substitution of alcohols is described. The salient features of this strategy include neutral and metal-free conditions for the rapid synthesis of sulfinates in high yields. The present protocol using p-toluenesulfonylmethyl isocyanide (TosMIC) and the triphenylphosphine (TPP)/diisopropyl azodicarboxylate (DIAD) reagent system represents the general synthetic route to this important class of compounds. (Figure presented.).
Discovery of a Type III Inhibitor of LIM Kinase 2 That Binds in a DFG-Out Conformation
Goodwin, Nicole C.,Cianchetta, Giovanni,Burgoon, Hugh A.,Healy, Jason,Mabon, Ross,Strobel, Eric D.,Allen, Jason,Wang, Shuli,Hamman, Brian D.,Rawlins, David B.
supporting information, p. 53 - 57 (2015/01/30)
The first allosteric, type III inhibitor of LIM-kinase 2 (LIMK2) is reported. A series of molecules that feature both an N-phenylsulfonamide and tertiary amide were not only very potent at LIMK2 but also were extremely selective against a panel of other k
