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 language | English |
|---|---|
| Pages (from-to) | 3510-3515 |
| Number of pages | 6 |
| Journal | Helvetica Chimica Acta |
| Volume | 86 |
| Issue number | 10 |
| DOIs | |
| State | Published - 2003 |
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Deng, G. H., Hu, H., Wei, H. X., & Paré, P. W. (2003). The Aldol Reaction of Allenolates with Aldehydes in the Presence of Magnesium Diiodide (MgI2) as Catalyst. Helvetica Chimica Acta, 86(10), 3510-3515. https://doi.org/10.1002/hlca.200390294