Irradiation of terminal aromatic gamma,delta-epoxy ketones with a 450 W UV lamp led to Norrish type II cyclization/semi-pinacol rearrangement cascade reaction which formed the benzocyclobutanones containing a full-carbon quaternary center, whereas irradiation of substituted aromatic gamma,delta-epoxy ketones led to the indanones through a photochemical epoxy rearrangement and 1,5-biradicals cyclization
Regio- and Enantioselective Copper-Catalyzed Allylic Alkylation of Ortho-Substituted Cinnamyl Bromides with Grignard Reagents
作者:Nathalie C. van der Molen、Theodora D. Tiemersma-Wegman、Martín Fañanás-Mastral、Ben L. Feringa
DOI:10.1021/acs.joc.5b00371
日期:2015.5.15
A highly efficient method for the copper-catalyzed asymmetric allylicalkylation of ortho-substituted cinnamyl bromides with Grignard reagents is reported. The use of a catalytic system comprising CuBr·SMe2 and TaniaPhos as chiral ligands gives rise to a range of branched products with excellent regio- and enantioselectivity.
A Synthetic Route to 2-Alkyl Indoles via Thiophenol-Mediated Ring-Opening of <i>N</i>-Tosylaziridines Followed by Copper Powder-Mediated C–N Cyclization/Aromatization
作者:Masthanvali Sayyad、Yerramsetti Nanaji、Manas K. Ghorai
DOI:10.1021/acs.joc.5b02251
日期:2015.12.18
A simple strategy for the syntheses of 2-alkyl indoles via regioselective ring-opening of 2-(2-haloaryl)-3-alkyl-N-tosylaziridines with thiophenol, followed by copper powder-mediated intramolecular C-N cyclization and subsequent aromatization by the elimination of thiophenol, with good yields is described. Utilizing this protocol, 2-carboxyindole has been synthesized easily.