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Efficient Addition of Acid Enediolates to Epoxides
Author(s) -
Gil Salvador,
Torres Mercedes,
Ortúzar Natalia,
Wincewicz Richard,
Parra Margarita
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300795
Subject(s) - chemistry , epoxide , lewis acids and bases , amine gas treating , stoichiometry , organic chemistry , catalysis
We report new conditions to facilitate the addition of dianions of carboxylic acids to epoxides as an alternative method to the use of aluminum enolates. These conditions require the use of a sub‐stoichiometric (10%) amount of amine for dianion generation and the previous activation of the epoxide with LiCl. Other Lewis acids have been shown to be less effective. Yields are good but only low diastereoselectivity is attained, which has not been controlled despite attempts at optimization. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)