Publication: Regioselectivity of the 1,3-Oxathiolane Formation in the Lewis Acid-Catalyzed Reaction of Thioketones with Asymmetrically Substituted Oxiranes
Regioselectivity of the 1,3-Oxathiolane Formation in the Lewis Acid-Catalyzed Reaction of Thioketones with Asymmetrically Substituted Oxiranes
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Fu, C., Linden, A., & Heimgartner, H. (2001). Regioselectivity of the 1,3-Oxathiolane Formation in the Lewis Acid-Catalyzed Reaction of Thioketones with Asymmetrically Substituted Oxiranes. Helvetica Chimica Acta, 84, 3319–3334. https://doi.org/10.1002/1522-2675(20011114)84:11<3319::AID-HLCA3319>3.0.CO;2-L
Abstract
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Abstract
The reactions of the aromatic thioketone 4,4'-dimethoxythiobenzophenone (1) with three monosubstituted oxiranes 3a - c in the presence of BF3 . Et2O or SnCl4 in dry CH2Cl2 led to the corresponding 1 : 1 adducts, i.e., 1,3- oxathiolanes 4a-b with R at C(5) and 8c with Ph at C(4). In addition, 1,3-dioxolanes 7a and 7c, and the unexpected 1 : 2 adducts 6a - b were obtained (Scheme 2 and Table 1) . In the case of the aliphatic, nonenolizable thioketone 1,1,3,3-tetramethylindane-2-thione (2) and 3a - c with BF3 . Et2O as catalyst, only 1 :
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- Fu, Changchun
- Heimgartner, Heinz
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Fu, C., Linden, A., & Heimgartner, H. (2001). Regioselectivity of the 1,3-Oxathiolane Formation in the Lewis Acid-Catalyzed Reaction of Thioketones with Asymmetrically Substituted Oxiranes. Helvetica Chimica Acta, 84, 3319–3334. https://doi.org/10.1002/1522-2675(20011114)84:11<3319::AID-HLCA3319>3.0.CO;2-L
