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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

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: msreddycdri.res.in

S. Puri, N. Thirupathi, M. S. Reddy, Org. Lett., 2014, 16, 5246-5249.

DOI: 10.1021/ol502224s (free Supporting Information)


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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

vinyl iodides, esters, iodine


ID: J54-Y2014