Samarium(II) Diiodide Induced Intramolecular Coupling Reaction of Haloacetals Leading to the Synthesis of γ-Lactones
- 1 January 1993
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1993 (10) , 803-804
- https://doi.org/10.1055/s-1993-22616
Abstract
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).Keywords
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