The Aldol Reaction of Allenolates with Aldehydes in the Presence of Magnesium Diiodide (MgI2) as Catalyst |
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Authors: | Guang‐Hui Deng,Hui Hu,Han‐Xun Wei,Paul W. Par |
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Affiliation: | 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). |
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