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Iodo Meyer-Schuster rearrangement of 3-alkoxy-2-yn-1-ols for β-mono (exclusively Z-selective)-/disubstituted α-iodo-α,β-unsaturated esters
Puri, Surendra,Thirupathi, Nuligonda,Reddy, Maddi Sridhar
, p. 5246 - 5249 (2015/02/19)
We herein present the iodo Meyer-Schuster rearrangement of 3-alkoxypropargyl alcohols for α-iodo-α,β-unsaturated esters using iodine or NIS in dichloromethane at ambient temperature. Substrates prepared from both aldehydes and ketones are found to be equally good feedstock for the reaction to produce β-mono-and-disubstituted products. Irrespective of the substitution, substrates prepared from aldehydes gave Z-isomers exclusively. (Chemical Equation Presented).
