Tetrahedron Letters

Organocatalytic head-to-tail dimerization of methacrolein via conjugate addition of methanol: an alcohol activation mechanism proved by electrospray ionization mass …

S Matsuoka, S Shimakawa, K Takagi, M Suzuki

Index: Matsuoka, Shin-Ichi; Shimakawa, Shintaro; Takagi, Koji; Suzuki, Masato Tetrahedron Letters, 2011 , vol. 52, # 50 p. 6835 - 6838

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Citation Number: 14

Abstract

The head-to-tail dimerization of methacrolein via the conjugate addition of methanol is catalyzed by various organic bases, such as an amine, phosphine, and N-heterocyclic carbene, to give 2, 4-dimethyl-2-methoxymethylpentane-1, 5-dial in moderate yields. Based on the interpretation of the key intermediates by electrospray ionization mass spectrometry, we propose a reaction mechanism involving the initial conjugate addition of the organic ...