2009
Suárez-Castillo Oscar R., Meléndez-Rodríguez Myriam, Morales-García Ana L., Cano-Escudero Indira C., Contreras-Martínez Yaneth M. A., Morales-Ríos Martha S., Joseph-Nathan Pedro . Synthesis of indolylindolines mediated by t-BuNH2 Heterocycles 78, 1463-1476 (2009). ISSN 0385-5414. DOI: 10.3987/COM-08-11627
Abstract
An improved synthesis of N1-carbomethoxylated indolylindolines 2 from 5-substituted indoles 1, by replacing the previously employed strong acids or toxic metals with t-BuNH2/MeOCOCl in CH2Cl2/H2O, is described. The substituent effect of electron donor or acceptor groups was examined, revealing that electron-deficient indoles are less reactive to dimerization than electron-rich indoles, with 5-cyano and 5-nitroindoles leading to no reaction. A dynamic process caused by the restricted rotation of the N-CO2Me bond of 2 was evidenced by 1H NMR measurements.
Transesterifications mediated by t-BuNH2
Stereochemical assignment of naturally occurring 2,3-epoxy-2-methylbutanoate esters
The absoluteconfiguration of cuauhtemone and related compounds
Synthesis of Bromoindole Alkaloids from Laurencia brongniartii
Trapping enols of esters and lactones with diazomethane
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Total Syntheses of Five Indole Alkaloids from the Marine Bryozoan Flustra foliacea
First Total Synthesis of ()-Flustraminol B
Configuration, stereodynamics and crystal structure of 3-substituted-2-oxofuro[2,3-b]indoles
Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine