Abstract
Imines 4 cyclize stereoselectively to dihydroindoles 2 upon use of a Li or Na alkoxide-alcohol combination. Depending on the type of alcohol applied either cis ( 2C ) or trans ( 2 T) spiroindolines 2 are formed. In case of imines 4 derived from electron-rich aromatic aldehydes the formation of 2 occurs also thermally. With Lewis acid/catalysis cyclization 4→2 proceeds in a less stereoselective manner. The stereochemistry of 2 follows from characteristic 1H and 13C NMR data.
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