Enantioenriched derivatives of N-allyl-o-iodoarylcarbamates undergo radical cyclizations to give enantioenriched dihydroindoles in 87-100% yields and 83-92% chirality transfers. Anionic cyclizations of these substrates proceed in 58-74% yields and 84-99% chirality transfers. N-Aryl barriers to rotation were measured and found to be comparable to similar o-iodoacetanilides. The radical and anionic cyclizations proceed with the same sense of chirality.In the cases where a hexane:EtOAc solvent system was used, the injections were monitored at wavelength 270 nm. All gas chromatography analysis was performed with an Agilent 6850 GC under the following conditions: Initial oven temp.
|Title||:||Mechanism and Chirality Transfer in Cyclizations of Amides and Related Compounds|
|Publisher||:||ProQuest - 2008|