4.8 Article

Gassman's Cationic [2+2] Cycloadditions Using Temporary Tethers

Journal

ORGANIC LETTERS
Volume 14, Issue 21, Pages 5562-5565

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol3026796

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Funding

  1. National Science Foundation [NSF-CHE1012198]
  2. Division Of Chemistry
  3. Direct For Mathematical & Physical Scien [1012198] Funding Source: National Science Foundation

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An intermolecular equivalent of Gassman's cationic [2 + 2] cycloaddition through the use of temporary tethering is described. Notably, hydrazine and hydroxyamide proved to be robust under the acidic conditions required for the cycloaddition, leading to unique cyclobutane manifolds in a highly regio- and stereoselective manner. This development represents a rare usage of hydrazine and hydroxyamide in the capacity as temporary tethers.

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