Remarkable electronic effect on the total stereoselectivity of the cycloaddition reaction of arylnitrile oxides with pyrrol-2-one derivatives

A Guesmi,N Ben Hamadi

doi:10.1515/hc-2019-0014

Abstract

AbstractThe regiospecific 1,3-dipolar cycloaddition of 1,5-dihydropyrrol-2-one and arylnitrile oxides derivatives have been investigated. The asymmetric induction expected by the chiral centre of the 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-one derivatives was very effective, single diastereoisomers anti-3 was formed. The diastereoselectivity was linked to the destabilization of the syn transition state as a result of the electrostatic repulsion between the hydroxy group of the dihydropyrrol-2-one derivatives and the atom oxygen of the dipole.

Highlights

The regiospecific 1,3-dipolar cycloaddition of 1,5-dihydropyrrol-2-one and arylnitrile oxides derivatives have been investigated
The diastereoselectivity was linked to the destabilization of the syn transition state as a result of the electrostatic repulsion between the hydroxy group of the dihydropyrrol-2-one derivatives and the atom oxygen of the dipole
As a continuation of our effort to utilize heterocyclic compounds as dipolarophiles in 1,3-dipolar cycloaddition reactions, we report the asymmetric 1,3-cycloaddition of aromatic nitrile oxides with pyrrol-2-one derivatives [12,13,14]

Summary

Introduction

Abstract: The regiospecific 1,3-dipolar cycloaddition of 1,5-dihydropyrrol-2-one and arylnitrile oxides derivatives have been investigated. The diastereoselectivity was linked to the destabilization of the syn transition state as a result of the electrostatic repulsion between the hydroxy group of the dihydropyrrol-2-one derivatives and the atom oxygen of the dipole. As a continuation of our effort to utilize heterocyclic compounds as dipolarophiles in 1,3-dipolar cycloaddition reactions, we report the asymmetric 1,3-cycloaddition of aromatic nitrile oxides with pyrrol-2-one derivatives [12,13,14].

Results

Conclusion