ORGN 57 |
| A catalytic Mitsunobu reaction system has been developed in which the azo reagent is used as an organocatalyst and iodosobenzene diacetate is used as the stoichiometric oxidant. In this system iodosobenzene diacetate oxidizes the formed hydrazine byproduct to regenerate the azo reagent. Yields obtained in the catalytic reactions using a variety of carboxylic acids and alcohols were slightly lower than those obtained from corresponding stoichiometric reactions. Both primary and secondary alcohols can be used as substrates in this reaction system, with the secondary alcohols affording products with inverted stereochemistry at the carbinol center. |
|
New Reactions and Methodology
1:30 PM-5:10 PM, Sunday, March 25, 2007 McCormick Place Lakeside -- Room E351, Level 3, Oral
Division of Organic Chemistry |