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Thiol-Catalyzed Acyl Radical Cyclization of Alkenals

2004; American Chemical Society; Volume: 70; Issue: 2 Linguagem: Inglês

10.1021/jo048275a

1520-6904

Kazuya Yoshikai, Tomoharu Hayama, Katsumi Nishimura, Ken‐ichi Yamada, Kiyoshi Tomioka,

Sulfur-Based Synthesis Techniques

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.