Several anti-6-substituted 1,3-dioxepan-5-ols were kinetically resolved using an immobilized lipase (Amano PS–C II) in toluenein the presence of vinyl acetate at 30 C. This approach provided, in some cases, the alcohol and the acetate in high enantiomericpurity, depending on the nature of the substituent (R = N3, SePh, I, OBn) and the acetal group (unsubstituted or dimethyl). The roleof the size of substituents is also discussed. Enantiopure anti-6-substituted 1,3-dioxepan-5-ols are useful building blocks.
Lipase-catalyzed resolution of anti-substituted 1,3-dioxepan-5-ols
RIELA, Serena;
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 toluenein the presence of vinyl acetate at 30 C. This approach provided, in some cases, the alcohol and the acetate in high enantiomericpurity, depending on the nature of the substituent (R = N3, SePh, I, OBn) and the acetal group (unsubstituted or dimethyl). The roleof the size of substituents is also discussed. Enantiopure anti-6-substituted 1,3-dioxepan-5-ols are useful building blocks.File in questo prodotto:
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Tetrahedron Asymmetry 17 (2006) 3128–3134.pdf
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