Tetrahedron Asymmetry p. 3283 - 3292 (1997)
Update date:2022-09-26
Topics:
Garcia Ruano, Jose L.
Gonzalez-Vadillo, Ana M.
Maestro, M. Carmen
The influence of the stereogenic hydroxylic carbon at the δ-position of the carbonyl group in 1,5-bis(p-tolylsulfinyl)-4-hydroxy-2-pentanone 1 and 2,6-bis(p-tolylsulfinyl)-5-hydroxy-3-hexanones 2 on the stereochemical course of DIBALH and DIBALH/ZnBr2 reductions has been studied. In contrast with the DIBALH reductions of β-hydroxyketones, that are monitored by the hydroxylic stereogenic carbon, the presence of the sulfinyl group determines a complete 1,3-induction of the sulfur centre.
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Doi:10.1016/j.tet.2020.131410
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