Phthalimides, reaction with lactones

Various electrophilic selenium reagents such as those described in Scheme 4.3 can be used. V-Phenylselenylphthalimide is an excellent reagent for this process and permits the formation of large ring lactones." The advantage of the reagent in this particular application is the low nucleophilicity of phthalimide, which does not compete with the remote internal nucleophile. The reaction of phenylselenenyl chloride or V-phenylselenenylphthalimide with unsaturated alcohols leads to formation of (3-phenylselenenyl ethers. 

N 0 Me 0 From hydroxymethyl polystyrene by treatment with COClj, HjNNHCOjMe and NBS or Cl,.2i Mitsunobu reactions esters from carboxylic acids and alcohols lactones from hydroxy acids A/-aUcylation of phthalimides, a-alkylation of cyanoacetate carbodiimides from thioureas. ... 

A lactone can be refunctionalized to an amino acid as well as a carboxylic acid. Reaction of 7.34 with potassium phthalimide opened the lactone ring to give a phthalimido-acid. Removal of the phthalimide group gave 2-methylamino-l-phenyl-cyclopropane-1-carboxylic acid, 7.35Amino acid 7.35 was tested as a potential antidepressant, and several aryl analogs were prepared the 4-chlorophenyl, the 4-methylphenyl, and the 4-methoxyphenyl derivatives. 

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