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Synlett 1993; 1993(10): 803-804
DOI: 10.1055/s-1993-22616
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Samarium(II) Diiodide Induced Intramolecular Coupling Reaction of Haloacetals Leading to the Synthesis of γ-Lactones

Shin-ichi Fukuzawa* , Teruhisa Tsuchimoto
  • *Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, Kasuga, Bunkyo-ku, Tokyo 112, Japan
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Publication Date:
19 March 2002 (online)

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Treatment of a mixture of a haloacetal (1) and tert-butanol with 2.5 equiv of samarium (II) diiodide in THF-HMPA gave in good conversion the cyclic acetal (2), which was transformed to the γ-lactone (3) with Jones oxidation (overall yield, 70-90 %). The stereochemistry of the 2,4-(2;R1=H, R2=Me, Et) or 2,3-disubustituted lactones were predominantly trans (trans: cis=86:14-98:2).

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