Highly regio- and stereoselective iodocyclization of chiral 3- alkoxycarbonyl-4-propenyl-2,2-dimethyl-1,3-oxazolidines: A computational investigation

Juan Miquel Jordá-Gregori, M. Eugenia González-Rosende, José Sepúlveda-Arques, Roberta Galeazzi, Mario Orena

Research output: Contribution to journalArticlepeer-review

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 languageEnglish
Pages (from-to)1135-1143
Number of pages9
JournalTetrahedron: Asymmetry
Volume10
Issue number6
DOIs
Publication statusPublished - Mar 26 1999

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

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