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.
| Original language | English |
|---|---|
| Pages (from-to) | 1135-1143 |
| Number of pages | 9 |
| Journal | Tetrahedron: Asymmetry |
| Volume | 10 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - Mar 26 1999 |
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ASJC Scopus subject areas
- Inorganic Chemistry
- Organic Chemistry
- Materials Chemistry
- Drug Discovery
Cite this
Highly regio- and stereoselective iodocyclization of chiral 3- alkoxycarbonyl-4-propenyl-2,2-dimethyl-1,3-oxazolidines : A computational investigation. / Jordá-Gregori, Juan Miquel; González-Rosende, M. Eugenia; Sepúlveda-Arques, José; Galeazzi, Roberta; Orena, Mario.
In: Tetrahedron: Asymmetry, Vol. 10, No. 6, 26.03.1999, p. 1135-1143.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Highly regio- and stereoselective iodocyclization of chiral 3- alkoxycarbonyl-4-propenyl-2,2-dimethyl-1,3-oxazolidines
T2 - A computational investigation
AU - Jordá-Gregori, Juan Miquel
AU - González-Rosende, M. Eugenia
AU - Sepúlveda-Arques, José
AU - Galeazzi, Roberta
AU - Orena, Mario
PY - 1999/3/26
Y1 - 1999/3/26
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0038607281&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0038607281&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(99)00084-1
DO - 10.1016/S0957-4166(99)00084-1
M3 - Article
AN - SCOPUS:0038607281
VL - 10
SP - 1135
EP - 1143
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 6
ER -