229318-68-7Relevant academic research and scientific papers
Highly regio- and stereoselective iodocyclization of chiral 3- alkoxycarbonyl-4-propenyl-2,2-dimethyl-1,3-oxazolidines: A computational investigation
Jorda-Gregori, Juan Miquel,Gonzalez-Rosende, M. Eugenia,Sepulveda-Arques, Jose,Galeazzi, Roberta,Orena, Mario
, p. 1135 - 1143 (1999)
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.
