A Cyclopropane Fragmentation Approach to Heterocycle Assembly: A Convergent Synthesis of Oxepanes
- 13 January 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (3) , 515-517
- https://doi.org/10.1021/ol047426t
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.Keywords
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