Flores Ferrándiz, Jesús, Chinchilla, Rafael
Solvent-dependent enantioswitching in the Michael addition of α,α-disubstituted aldehydes to maleimides organocatalyzed by mono-N-Boc-protected cyclohexa-1,2-diamines
Tetrahedron: Asymmetry. 2014, 25(15): 1091-1094. doi:10.1016/j.tetasy.2014.06.014
URI: http://hdl.handle.net/10045/46332
DOI: 10.1016/j.tetasy.2014.06.014
ISSN: 0957-4166 (Print)
Abstract: 
Enantiomerically pure mono-N-Boc-protected trans-cyclohexa-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to maleimides. Using a single enantiomer of the organocatalyst, both enantiomeric forms of the resulting Michael adducts bearing a new quaternary stereocenter are obtained in high yields, by only changing the reaction solvent from chloroform (up to 86% ee) to aqueous DMF (up to 84% ee).
Keywords:Organocatalysts, Enantioselective, Michael addition, α,α-disubstituted aldehydes, Maleimides
Elsevier
info:eu-repo/semantics/article