A cyclopropane fragmentation approach to heterocycle assembly: a convergent synthesis of oxepanes |
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Authors: | O'Neil Kerry E Kingree Seth V Minbiole Kevin P C |
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Affiliation: | Department of Chemistry, James Madison University, Harrisonburg, VA 22807, USA. |
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Abstract: | [reaction: see text] A cyclopropanol fragmentation approach to the synthesis of oxepanes has been developed. This convergent strategy condenses cyclopropyl diols with aldehydes to form an acetal, which is subsequently rearranged to furnish a keto-oxepane. The reaction has been developed as a one-pot procedure, utilizing sequential addition of Al(OTf)3 and TiCl4. Yields range from 50 to 70% for the sequence. A Zimmerman-Traxler transition state disposing substituents in equatorial positions is consistent with the observed formation of strictly cis products. |
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