Synfacts 2006(12): 1249-1249  
DOI: 10.1055/s-2006-949498
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cascade Radical Addition-Cyclization-Trapping Reactions

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
H. Miyabe*, R. Asada, A. Toyoda, Y. Takemoto*
Kyoto University, Japan
Further Information

Publication History

Publication Date:
22 November 2006 (online)

Significance

An enantioselective radical cyclization reaction is described. The authors found that the use of zinc triflate at -78 °C was necessary to hold the substrate in the appropriate conformation to obtain high diastereoselectivity and enantioselectivity. Secondary alkyl iodides were used as radical acceptors and were able to trap the substrate’s primary radical that was formed after cyclization.