Diastereochemical diversity of imidazoline scaffolds via substrate controlled TMSCl mediated cycloaddition of azlactones

Vasudha Sharma; Jetze J Tepe

doi:10.1021/ol052118w

Diastereochemical diversity of imidazoline scaffolds via substrate controlled TMSCl mediated cycloaddition of azlactones

Org Lett. 2005 Oct 27;7(22):5091-4. doi: 10.1021/ol052118w.

Authors

Vasudha Sharma¹, Jetze J Tepe

Affiliation

¹ Department of Chemistry, Michigan State University, East Lansing, 48823, USA.

PMID: 16235965
DOI: 10.1021/ol052118w

Abstract

[reaction: see text] We report herein a trimethylsilyl chloride mediated substrate controlled 1,3-dipolar cycloaddition for the diastereoselective synthesis of either syn- or anti-imidazolines. This method provides scaffolds with four points of diversity and control over two stereocenters.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Cyclization
Imidazolines / chemical synthesis*
Imidazolines / chemistry
Lactones / chemistry*
Molecular Structure
Stereoisomerism
Trimethylsilyl Compounds / chemistry*

Substances

Imidazolines
Lactones
Trimethylsilyl Compounds