Iodo Meyer-Schuster Rearrangement of 3-Alkoxy-2-yn-1-ols for β-Mono (Exclusively Z-Selective)-/Disubstituted α-Iodo-α,β-Unsaturated Esters
Surendra Puri, Nuligonda Thirupathi and Maddi Sridhar Reddy*
*Medicinal & Process Chemistry Division, CSIR-Central Drug
Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O.
Box 173, Lucknow 226031, India, Email: msreddy
cdri.res.in
S. Puri, N. Thirupathi, M. S. Reddy, Org. Lett., 2014, 16, 5246-5249.
DOI: 10.1021/ol502224s
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Abstract
An iodo Meyer-Schuster rearrangement of 3-alkoxypropargyl alcohols using iodine or NIS in dichloromethane at ambient temperature produces α-iodo-α,β-unsaturated esters in good yields. Secondary alcohols gave Z-isomers exclusively.
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Key Words
ID: J54-Y2014
