Abstract
The iodocyclization of allylic carbamates 3a and 3b proceeded with high regio- and stereoselection to give 2-oxobicyclo[4.3.0]nonane 5a as the major product. Both the regio- and diastereoselection of the reaction were investigated with the help of molecular mechanics and quantomechanical calculations. The energetic difference between the competing transition states TS- 5a and TS- 5b is in good agreement with the experimental results and from the calculated transition structures it appears that steric factors direct the discrimination.
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