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 journalArticle

21 Citations (Scopus)

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

Fingerprint

Molecular mechanics
Carbamates
Mechanics
nonanes
discrimination
products
nonane
oxazolidine

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 journalArticle

Jordá-Gregori, Juan Miquel ; González-Rosende, M. Eugenia ; Sepúlveda-Arques, José ; Galeazzi, Roberta ; Orena, Mario. / Highly regio- and stereoselective iodocyclization of chiral 3- alkoxycarbonyl-4-propenyl-2,2-dimethyl-1,3-oxazolidines : A computational investigation. In: Tetrahedron: Asymmetry. 1999 ; Vol. 10, No. 6. pp. 1135-1143.
@article{eca7681fc04e4e3783318a506bcaaac9,
title = "Highly regio- and stereoselective iodocyclization of chiral 3- alkoxycarbonyl-4-propenyl-2,2-dimethyl-1,3-oxazolidines: A computational investigation",
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.",
author = "Jord{\'a}-Gregori, {Juan Miquel} and Gonz{\'a}lez-Rosende, {M. Eugenia} and Jos{\'e} Sep{\'u}lveda-Arques and Roberta Galeazzi and Mario Orena",
year = "1999",
month = "3",
day = "26",
doi = "10.1016/S0957-4166(99)00084-1",
language = "English",
volume = "10",
pages = "1135--1143",
journal = "Tetrahedron Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Limited",
number = "6",

}

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 -