Unusual regioselectivity in the opening of epoxides by carboxylic acid enediolates.
Addition of carboxylic acid dianions appears to be a potential alternative to the use of aluminium enolates for nucleophilic ring opening of epoxides. These conditions require the use of a sub-stoichiometric amount of amine (10% mol) for dianion generation and the previous activation of the epoxide with LiCl. Yields are good, with high regioselectivity, but the use of styrene oxide led, unexpectedly, to a mixture resulting from the attack on both the primary and secondary carbon atoms. Generally, a low diastereoselectivity is seen on attack at the primary center, however only one diastereoisomer was obtained from attack to the secondary carbon of the styrene oxide.
Domingo
Luis R
LR
Department of Organic Chemistry, Universitat de València, Dr. Moliner 50, 46100 Burjassot, Spain.
Gil
Salvador
S
Parra
Margarita
M
Segura
José
J
D002264:Carboxylic Acids / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*
D002264:Carboxylic Acids; D004852:Epoxy Compounds; C013690:styrene oxide