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Synfacts 2006(7): 0688-0688  
DOI: 10.1055/s-2006-941818
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

(-)-Emetine Synthesis via Asymmetric Allylation of Cyclic Imines

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Itoh*, M. Miyazaki, H. Fukuoka, K. Nagata, A. Ohsawa
Showa University, Tokyo, Japan
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

While there are a few reports for the asymmetric allylation of imines, the addition of allyl substrates to cyclic imines remains a challenge. Using conditions similar to a report by Shibasaki and co-workers (J. Am. Chem. Soc. 2002, 124, 6536-6537), the authors obtained their desired product in 91% yield and 71% ee. One recrystallization with (-)-di­benzoyl-l-tartaric acid afforded their compound with 97% ee. This compound was then carried on to complete the synthesis of (-)-Emetine.