Isocyanoacetates as substrates for enantioselective addition and cycloaddition reactions

Abstract

In this thesis, different addition and cycloaddition reactions involving the use of isocyanoacetates as substrates are presented. These approaches allow for the synthesis of highly-functionalized isonitrile-containing compounds as well as the obtention of aza-heterocycles, respectively. The showcased reactions include 1) the alpha-arylation of isocyanoacetate esters by their 1,4-addition to o-quinone dibenzimides; 2) the organocatalytic conjugate addition of isocyanoacetate esters to aurone-derived 1-azadienes; 3) the enantioselective dearomative formal [3+2] cycloaddition of 2-nitrobenzofurans and isocyanoacetates; and 4) the enantioselective [3+3] cycloaddition of isocyanoacetates and N-iminoquinazolinium ylides.