Publication: Regio- and stereoselectivity in the Lewis acid- and NaH-induced reactions of thiocamphor with (R)-2-vinyloxirane
Regio- and stereoselectivity in the Lewis acid- and NaH-induced reactions of thiocamphor with (R)-2-vinyloxirane
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Fedorov, A., Fu, C., & Heimgartner, H. (2006). Regio- and stereoselectivity in the Lewis acid- and NaH-induced reactions of thiocamphor with (R)-2-vinyloxirane. Helvetica Chimica Acta, 89(3), 456–467. https://doi.org/10.1002/hlca.200690046
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The reaction of the enolizable thioketone (1R,4R)-thiocamphor (=(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-thione; 1) with (R)-2-vinyloxirane (2) in the presence of a Lewis acid such as SnCl4 or SiO2 in anhydrous CH2Cl2 gave the spirocyclic 1,3-oxathiolane 3 with the vinyl group at C(4’), as well as the isomeric enesulfanyl alcohol 4. In the case of SnCl4, an allylic alcohol 5 was obtained in low yield in addition to 3 and 4 (Scheme 2). Repetition of the reaction in the presence of ZnCl2 yielded two diastereoisomeric 4-vinyl-1,3-o
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- Fedorov, A
- Fu, C
- Heimgartner, H
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Fedorov, A., Fu, C., & Heimgartner, H. (2006). Regio- and stereoselectivity in the Lewis acid- and NaH-induced reactions of thiocamphor with (R)-2-vinyloxirane. Helvetica Chimica Acta, 89(3), 456–467. https://doi.org/10.1002/hlca.200690046
