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Synfacts 2008(2): 0179-0179  
DOI: 10.1055/s-2007-992452
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Samarium(II) Iodide Catalyzed One-Pot Aza-Diels-Alder Reactions

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
Z. Zhou, F. Xu*, X. Han, J. Zhou, Q. Shen*
Suzhou University, P. R. of China
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

The authors describe a three-component aza-Diels-Alder reaction that is catalyzed by samarium(II) iodide. Interestingly, the cis/trans isomer issue can be controlled by the reaction conditions. When the reaction is conducted in organic solvents, the trans isomer is favored. Under solvent-less conditions, the cis isomer predominates. Higher temperatures were also found to give high yields of the trans product, while lower temperatures increased the cis selectivity.