Volume 31, Issue 7
Natural Products
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ChemInform Abstract: Asymmetric Cyclization of meso-Diepoxides Using Chiral (Salen)Co(III)OAc Catalyst Forming Optically Active 1,4-Anhydropentitols and 2,5-Anhydrohexitols.

Masatoshi Kamada

Masatoshi Kamada

Div. Mol. Chem., Grad. Sch. Eng., Hokkaido Univ., Sapporo 060, Japan

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Toshifumi Satoh

Toshifumi Satoh

Div. Mol. Chem., Grad. Sch. Eng., Hokkaido Univ., Sapporo 060, Japan

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Toyoji Kakuchi

Toyoji Kakuchi

Div. Mol. Chem., Grad. Sch. Eng., Hokkaido Univ., Sapporo 060, Japan

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Kazuaki Yokota

Kazuaki Yokota

Div. Mol. Chem., Grad. Sch. Eng., Hokkaido Univ., Sapporo 060, Japan

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First published: 10 June 2010

Abstract

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ChemInform Abstract

Asymmetric hydration of meso-diepoxides (I) and (III) in the presence of a chiral Co—salen complex proceeds with high enantioselectivity (>99% e.e.) to furnish 1,4-anhydropentitol (II) and 2,5-anhydrohexitol (IV), resp., in good yields. In the case of compound (III), the cyclization reaction is not totally regioselective and 1,5-anhydrohexitol (V) is obtained as side product.

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