Asymmetric Organocatalytic Stepwise [2+2] Entry to Tetra‐Substituted Heterodimeric and Homochiral Cyclobutanes |
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| Authors: | Alex J. Nielsen Dr. Hilary A. Jenkins Dr. James McNulty |
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| Affiliation: | 1. Department of Chemistry and Chemical-Biology, McMaster University, Hamilton, Ontario, Canada;2. http://www.chemistry.mcmaster.ca/mcnulty/index.html |
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| Abstract: | An asymmetric synthesis of tetra‐substituted cyclobutanes involving an organocatalytic, stepwise [2+2]‐cycloaddition is described. The secondary‐amine‐catalyzed method allows for the hetero‐dimerization of two different cinnamic‐acid‐derived sub‐units, opening a novel one‐step assembly to densely functionalized, head‐to‐tail coupled dimeric cyclobutanes in high enantiomeric excess. A series of selective synthetic interconversions in these sensitive cycloadducts is also described. |
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| Keywords: | asymmetric synthesis cyclobutanes lignan dimers organocatalysis |
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