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  • Title: Highly regio- and stereoselective cyclic iodoetherification of 4,5-alkadienols. An efficient preparation of 2-(1'(Z)-iodoalkenyl)tetrahydrofurans.
    Author: Lü B, Jiang X, Fu C, Ma S.
    Journal: J Org Chem; 2009 Jan 02; 74(1):438-41. PubMed ID: 19053197.
    Abstract:
    In this paper, an efficient way to synthesize 2-(1'(Z)-iodoalkenyl)tetrahydrofurans from 4,5-alkadienols and I(2) was developed. The reaction of the 4,5-allenols with a substituent in the 3-position afforded the trans-2,3-disubstituted tetrahydrofurans with very high diastereoselectivity. However, when the axially optically active 4,5-allenol was treated with I(2) in n-hexane, the efficiency for chirality transfer was low. This problem was circumvented by conducting the reaction in CH(2)Cl(2) at room temperature and applying N-iodosuccinimide as the electrophilic reagent; however, the Z/E ratio for the products is much lower. Highly optically active Z-products may be prepared via the kinetic resolution via a Sonogashira coupling reaction with propargyl alcohol.
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