Nishino Fumiaki, Miki Koji, Kato Yumiko, Ohe Kouichi, Uemura Sakae
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Org Lett. 2003 Jul 24;5(15):2615-7. doi: 10.1021/ol0347545.
[reaction: see text] The reaction of alkenes with conjugated ene-yne-imino ether or ene-yne-aldimine in the presence of a catalytic amount of Rh(OAc)(2) gives (2-pyrrolyl)cyclopropanes in good yields. The key intermediate of this cyclopropanation is a (2-pyrrolyl)carbenoid generated by the nucleophilic attack of imine nitrogen atom at an internal alkyne carbon activated by rhodium complex. The intramolecular reaction also proceeds to afford a polycyclic pyrrole.
