Molecules 2008, 13(6), 1303-1311; doi:10.3390/molecules13061303
Communication

Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates

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Received: 29 May 2008; in revised form: 5 June 2008 / Accepted: 6 June 2008 / Published: 9 June 2008
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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