Publication: Reaction of optically active Oxiranes with Thiofenchone and 1-Methylpyrrolidine-2-thione. Formation of 1,3-Oxathiolanes and Thiiranes
Reaction of optically active Oxiranes with Thiofenchone and 1-Methylpyrrolidine-2-thione. Formation of 1,3-Oxathiolanes and Thiiranes
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Fu, C., Linden, A., & Heimgartner, H. (2011). Reaction of optically active Oxiranes with Thiofenchone and 1-Methylpyrrolidine-2-thione. Formation of 1,3-Oxathiolanes and Thiiranes. Helvetica Chimica Acta, 94(5), 773–784. https://doi.org/10.1002/hlca.201100043
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The SnCl4-catalyzed reaction of (-)-thiofenchone (= 1,3,3-trimethyl-bicyclo[2.2.1]heptane-2-thione;10) with (R)-2-phenyloxirane ((R)-11) in anhydrous CH2Cl2 at -60° led to two spirocyclic, stereoisomeric 4-phenyl-1,3-oxathiolanes 12 and 13 via a regioselective ring enlargement, in accordance with previously reported reactions of oxiranes with thioketones (Scheme 3). The structure and configuration of the major isomer 12 were determined by X-ray crystallography. On the other hand, the reaction of 1- methylpyrrolidine-2-thione (14a) wi
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- Fu, C
- Heimgartner, H
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Fu, C., Linden, A., & Heimgartner, H. (2011). Reaction of optically active Oxiranes with Thiofenchone and 1-Methylpyrrolidine-2-thione. Formation of 1,3-Oxathiolanes and Thiiranes. Helvetica Chimica Acta, 94(5), 773–784. https://doi.org/10.1002/hlca.201100043
