Several anti-6-substituted 1,3-dioxepan-5-ols were kinetically resolved using an immobilized lipase (Amano PS–C II) in toluene in the presence of vinyl acetate at 30 C. This approach provided, in some cases, the alcohol and the acetate in high enantiomeric purity, depending on the nature of the substituent (R = N3, SePh, I, OBn) and the acetal group (unsubstituted or dimethyl). The role of the size of substituents is also discussed. Enantiopure anti-6-substituted 1,3-dioxepan-5-ols are useful building blocks.
GRUTTADAURIA M, LO MEO P, RIELA S, GIACALONE F, NOTO R (2006). Lipase-catalyzed resolution of anti-substituted 1,3-dioxepan-5-ols. TETRAHEDRON-ASYMMETRY, 17, 3128-3134 [10.1016/j.tetasy.2006.11.024].
Lipase-catalyzed resolution of anti-substituted 1,3-dioxepan-5-ols
GRUTTADAURIA, Michelangelo
;LO MEO, Paolo Maria Giuseppe;RIELA, Serena;GIACALONE, Francesco;NOTO, Renato
2006-01-01
Abstract
Several anti-6-substituted 1,3-dioxepan-5-ols were kinetically resolved using an immobilized lipase (Amano PS–C II) in toluene in the presence of vinyl acetate at 30 C. This approach provided, in some cases, the alcohol and the acetate in high enantiomeric purity, depending on the nature of the substituent (R = N3, SePh, I, OBn) and the acetal group (unsubstituted or dimethyl). The role of the size of substituents is also discussed. Enantiopure anti-6-substituted 1,3-dioxepan-5-ols are useful building blocks.
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