The Lewis acid-catalyzed [3+1+1] cycloaddition of azomethine ylides with isocyanides

• DOI: 10.1016/j.tet.2014.06.118
• Publication Date: 2014-07-03T17:04:08Z
• Authors: Takahiro Soeta; Yoshiaki Miyamoto; Shuhei Fujinami; Yutaka Ukaji
• Keywords: 01 natural sciences; 0104 chemical sciences

Abstract A Lewis acid-catalyzed [3+1+1] cycloaddition reaction between aliphatic isocyanides and azomethine ylides generated in situ from aziridines, leading to pyrrolidine derivatives, has been developed. This reaction proceeds smoothly under mild conditions and can also be modified by employing aromatic isocyanides to generate four-membered heterocycles, azetidines, through a [3+1] cycloaddition reaction.