6533b86dfe1ef96bd12c9de3
RESEARCH PRODUCT
Highly regio- and stereoselective iodocyclization of chiral 3-alkoxycarbonyl-4-propenyl-2,2-dimethyl-1,3-oxazolidines: a computational investigation
José Sepúlveda-arquesM. Eugenia González-rosendeRoberta GaleazziJuan Miquel Jordá-gregoriMario Orenasubject
PropenylSteric effectsAllylic rearrangementStereochemistryChemistryOrganic ChemistryMedicinal chemistryCatalysisTransition stateInorganic Chemistrychemistry.chemical_compoundStereoselectivityPhysical and Theoretical ChemistryNonanedescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1999-03-01 | Tetrahedron: Asymmetry |