New regiospecific synthesis of tri- and tetra-substituted furans.
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.
Sydnes
Leiv K
LK
Department of Chemistry, University of Bergen, Allegt 41, NO-5007 Bergen, Norway. leiv.sydnes@kj.uib.no
Holmelid
Bjarte
B
Sengee
Myagmarsuren
M
Hanstein
Miriam
M