Organic Chemistry Portal

Abstracts

Search:

Stereoselective Formation of Alkenyl Halides via Magnesium Halide Promoted Ring Opening of Bis-Activated Cyclopropenes

Yi Wang and Hon Wai Lam*

*School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, United Kingdom, Email: h.lamed.ac.uk

Y. Wang, H. W. Lam, J. Org. Chem., 2009, 74, 1353-1355.

DOI: 10.1021/jo802475x (free Supporting Information)


Abstract

Various bis-activated cyclopropenes undergo highly stereoselective ring-opening reactions to produce multisubstituted alkenyl halides in the presence of stoichiometric magnesium halides. Trapping of the magnesium enolate intermediates in situ allows the synthesis of highly functionalized compounds.


see article for more examples

see article for more reactions



Key Words

Cyclopropenes, Alkenyl Iodides, Alkenyl Bromides, Alkenyl Chlorides, 1,4-Additions, Multicomponent Reactions


ID: J42-Y2009-0420