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Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates
Department of Organic Chemistry, Universitat de València, Dr. Moliner 50, 46100 Burjassot, Spain; Fax +34(9)63543831
* Author to whom correspondence should be addressed.
Received: 29 May 2008; in revised form: 5 June 2008 / Accepted: 6 June 2008 / Published: 9 June 2008
Abstract: 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.
Keywords: Lactones; lithium chloride; nucleophilic addition; regioselectivity; diastereoselectivity.
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Domingo, L.R.; Gil, S.; Parra, M.; Segura, J. Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates. Molecules 2008, 13, 1303-1311.
Domingo LR, Gil S, Parra M, Segura J. Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates. Molecules. 2008; 13(6):1303-1311.
Domingo, Luis R.; Gil, Salvador; Parra, Margarita; Segura, José. 2008. "Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates." Molecules 13, no. 6: 1303-1311.