Diastereoselective Radical Tandem Addition-Cyclization Reactions of Aromatic Tertiary Amines by Semiconductor-Sensitized Photochemical Electron Transfer

✍ Scribed by Siniša Marinković; Norbert Hoffmann

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 140 KB
• Volume: 2004
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200400102

✦ Synopsis

Abstract

The diastereoselective radical tandem addition‐cyclization reaction of N,N‐dimethylaniline (2) with menthyloxyfuranone 1 was initiated by photochemically induced electron transfer using inorganic semiconductors (TiO~2~, ZnS, SiC and SnO~2~) as sensitizers. The rearomatization step, which also causes the partial reduction of 1, was studied by isotopic labeling experiments using deuterated derivatives of 2. The influence of the semiconductor surface on these processes has been characterized and compared with the results obtained under homogeneous conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)