New regiospecific synthesis of tri- and tetra-substituted furans

Leiv K Sydnes; Bjarte Holmelid; Myagmarsuren Sengee; Miriam Hanstein

doi:10.1021/jo9003986

New regiospecific synthesis of tri- and tetra-substituted furans

J Org Chem. 2009 May 1;74(9):3430-43. doi: 10.1021/jo9003986.

Authors

Leiv K Sydnes¹, Bjarte Holmelid, Myagmarsuren Sengee, Miriam Hanstein

Affiliation

¹ Department of Chemistry, University of Bergen, Allegt 41, NO-5007 Bergen, Norway. leiv.sydnes@kj.uib.no

PMID: 19344132
DOI: 10.1021/jo9003986

Abstract

Beta-acyloxy alpha,beta-unsaturated acetylenic ketones have been shown to react with organocuprate reagents and undergo cyclization followed by dehydration to give substituted furans as the final products. The transformation appeared to be versatile, and tri- and tetra-substituted furans were obtained with regiochemical control in moderate to good yields. The best yields were generally obtained when the reactions were performed around -60 degrees C with substrates and cuprates containing sterically demanding substituents. The proposed mechanism for furan formation has been supported by experiments.