Catalytic Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes by a Simple Thiourea Organocatalyst

Raquel P. Herrera, Valentina Sgarzani, Luca Bernardi, Alfredo Ricci. Catalytic Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes by a Simple Thiourea Organocatalyst. Angew. Chem. Int. Ed. . 2005, Vol. 44 / 2005, p. 6576-2005.

The first catalytic enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes is described. Nitroalkenes are activated for addition through H-bonding interactions with a simple thiourea organocatalyst, easily accessible in both enantiomeric forms. This reaction provides an easy and practical access to highly valuable 2-indolyl-1-nitro derivatives in fairly good yields and with moderate to good enantioselectivities