Thiol-catalyzed acyl radical cyclization of alkenals.
Thiol-catalyzed direct generation of acyl radicals and their intramolecular addition to olefins of alkenals gave 2-substituted five- and six-membered cyclic ketones in reasonably good yields. The combination of odorless tert-dodecanthiol and AIBN or V-40 was the initiator of choice among surveyed radical generators for the cyclization of alkenals. Aldehydes having electron-deficient olefins cyclized more easily than those having unactivated olefins.
Yoshikai
Kazuya
K
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Hayama
Tomoharu
T
Nishimura
Katsumi
K
Yamada
Ken-Ichi
K
Tomioka
Kiyoshi
K