Asymmetric Friedel-Crafts alkylation of pyrrole with nitroalkenes catalyzed by a copper complex of a bisphenol A-derived Schiff base

作者：Ozdemir Halide Sedef; Sahin Engin; Cakici Murat; Kilic Hamdullah^*

来源：Tetrahedron, 2015, 71(19): 2882-2890.

DOI：10.1016/j.tet.2015.03.059

• Chiral copper complex
• Pyrrole
• Nitroalkene
• Asymmetric Friedel-Crafts alkylation
• Asymmetric synthesis

The asymmetric Friedel-Crafts (FC) alkylation of pyrrole with nitroalkenes was mediated by CuBr2 and a novel bisphenol A-derived chiral catalyst at room temperature. The catalyst was found to be applicable for the asymmetric FC alkylation of pyrrole with a wide range of nitroalkenes, affording optically active alkylated pyrroles with enantioselectivities up to 94%. Furthermore, enantiomerically pure 3-nitro-2-arylpropanamides were prepared by the oxidative cleavage of the pyrrole rings in the FC products with NaIO4/RuCl3 to demonstrate the synthetic application of the products.

• 出版日期2015-5-13