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Synthesis of Substituted α-(Hydroxymethyl)-β-iodoacrylates via MgI2-Promoted Stereoselective Aldol Coupling

✍ Scribed by Han-Xun Wei; Jiali Hu; Richard L. Jasoni; Guigen Li; Paul W. Paré

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
111 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 conditions, promoted by MgI~2~, which serves both as a Lewis acid and iodine source for a BaylisHillman‐type reaction. All adducts were generated in good‐to‐excellent yields, the (Z)‐isomers being formed in high selectivity (>98%). The conversion of methyl prop‐2‐ynoate into an active ‘β‐iodo allenolate’ intermediate, which then nucleophilically attacks an aldehyde, is proposed as a plausible reaction mechanism.

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