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Stereoselective aldol coupling of α,β-acetylenic ketones promoted by MgI2

✍ Scribed by Han-Xun Wei; Jiali Hu; David W. Purkiss; Paul W. Paré

Book ID
104252827
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
290 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

A highly stereoselective synthesis of (Z)-b-iodovinyl ketone has been achieved with the tandem formation of C C and C I bonds in a three-component reaction. This new catalysis utilizes MgI 2 as a Lewis acid as well as an iodine source for a Michael-type addition. a,b-Acetylenic ketone is initially converted to an active b-iodo allenolate intermediate and then can be attacked by a variety of aldehydes to afford Z-selective Baylis-Hillman adducts in excellent yields.

📜 SIMILAR VOLUMES

Synthesis of Substituted α-(Hydroxymethy
Synthesis of Substituted α-(Hydroxymethyl)-β-iodoacrylates via MgI2-Promoted Stereoselective Aldol Coupling
✍ Han-Xun Wei; Jiali Hu; Richard L. Jasoni; Guigen Li; Paul W. Paré 📂 Article 📅 2004 🏛 John Wiley and Sons 🌐 German ⚖ 111 KB

## Abstract The efficient and highly stereoselective syntheses of a variety of (__Z__)‐configured, substituted __α__‐(hydroxymethyl)**‐**__β__‐iodo‐acrylates from prop‐2‐ynoate and various aldehydes was achieved. The synthetic protocol involves a simple one‐pot coupling reaction under mild conditio