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.
2006
Settore CHIM/06 - Chimica Organica
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].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/19304
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