TY - JOUR
T1 - Synthesis of substituted α-(hydroxymethyl)-β-iodoacrylates via MgI2-promoted stereoselective aldol coupling
AU - Wei, Han Xun
AU - Hu, Jiali
AU - Jasoni, Richard L.
AU - Li, Guigen
AU - Paré, Paul W.
PY - 2004
Y1 - 2004
N2 - 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 MgI2, 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.
AB - 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 MgI2, 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.
UR - http://www.scopus.com/inward/record.url?scp=5644224476&partnerID=8YFLogxK
U2 - 10.1002/hlca.200490212
DO - 10.1002/hlca.200490212
M3 - Article
AN - SCOPUS:5644224476
SN - 0018-019X
VL - 87
SP - 2359
EP - 2363
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 9
ER -