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Thiol-Catalyzed Acyl Radical Cyclization of Alkenals

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Kazuya Yoshikai, Tomoharu Hayama, Katsumi Nishimura, Ken-ichi Yamada, and Kiyoshi Tomioka*

Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan tomioka@pharm.kyoto-u.ac.jp

J. Org. Chem., 2005, 70 (2), pp 681–683

DOI: 10.1021/jo048275a

Publication Date (Web): December 15, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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.

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Published In Issue January 21, 2005
Received September 30, 2004

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Thiol-Catalyzed Acyl Radical Cyclization of Alkenals

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

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