Molecules

Unusual regioselectivity in the opening of epoxides by carboxylic acid enediolates

LR Domingo, S Gil, M Parra, J Segura

Index: Domingo, Luis R.; Gil, Salvador; Parra, Margarita; Segura, Jose Molecules, 2008 , vol. 13, # 6 p. 1303 - 1311

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Citation Number: 6

Abstract

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 ...