The Aldol Reaction of Allenolates with Aldehydes in the Presence of Magnesium Diiodide (MgI2) as Catalyst

Guang Hui Deng, Hui Hu, Han Xun Wei, Paul W. Paré

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Abstract

Stereoselective synthesis of (Z)-α-(hydroxyalkyl)-β -iodoacrylates (=(2Z)-2-(hydroxyalkyl)-3-iodoprop-2-enoates) was achieved in a one-pot coupling reaction from methyl prop-2-ynoate, Me3SiI, and an alkanal under mild conditions with MgI2 as catalyst (→ 1-9; see Table and Scheme 1). Baylis-Hillman β-iodo adducts were generated in excellent yields with high (Z)-selectivity. The conversion of methyl prop-2-ynoate to an active methyl 3-iodo-1-[(trimethylsilyl)oxy]allenolate intermediate in situ followed by carbonyl addition is proposed as the reaction sequence (Schemes 1 and 2).

Original languageEnglish
Pages (from-to)3510-3515
Number of pages6
JournalHelvetica Chimica Acta
Volume86
Issue number10
DOIs
StatePublished - 2003

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