One-Pot Approach to the Conversion of Alcohols into α-Iodo-α,β-unsaturated Esters

Abstract

(Carboethoxymethylene)triphenylphosphorane 1 can undergo the tandem reaction of iodination–oxidation–Wittig reaction with alcohol in the presence of N-iodosuccinimide (NIS) and manganese dioxide. The reaction constitutes a stereoselective one-pot procedure for the preparation of Z-configured α-iodo-α,β-unsaturated esters in good to excellent yield.

Keywords:

• α-Iodo-α,β-unsaturated esters
• iodoylides
• one-pot synthesis
• oxidation

ACKNOWLEDGMENT

I thank the Saudi Basic Industries Corporation (SABIC) for financial support (Project Science-5–2007).

Notes

^a Yields were based on alcohols.

^b This ratio was determined by ¹H NMR spectroscopy.