Volume 31, Issue 51
Heterocyclic Compounds
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ChemInform Abstract: Stereospecific Synthesis of α,ω-cis- and α,ω-trans-Disubstituted Oxepanes.

Ryuji Matsumura

Ryuji Matsumura

Grad. Sch. Sci. Technol., Niigata Univ., Ikarashi, Niigata 950-21, Japan

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Toshio Suzuki

Toshio Suzuki

Grad. Sch. Sci. Technol., Niigata Univ., Ikarashi, Niigata 950-21, Japan

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Kohki Sato

Kohki Sato

Grad. Sch. Sci. Technol., Niigata Univ., Ikarashi, Niigata 950-21, Japan

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Takashi Inotsume

Takashi Inotsume

Grad. Sch. Sci. Technol., Niigata Univ., Ikarashi, Niigata 950-21, Japan

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Hisahiro Hagiwara

Hisahiro Hagiwara

Grad. Sch. Sci. Technol., Niigata Univ., Ikarashi, Niigata 950-21, Japan

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Takashi Hoshi

Takashi Hoshi

Grad. Sch. Sci. Technol., Niigata Univ., Ikarashi, Niigata 950-21, Japan

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Vijayendra P. Kamat

Vijayendra P. Kamat

Grad. Sch. Sci. Technol., Niigata Univ., Ikarashi, Niigata 950-21, Japan

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Masayoshi Ando

Masayoshi Ando

Grad. Sch. Sci. Technol., Niigata Univ., Ikarashi, Niigata 950-21, Japan

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First published: 31 May 2010

Abstract

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ChemInform Abstract

Reaction of trans-epoxides such as (I) or (III) with (Bu3Sn)2O results in formation of tin ethers. Subsequent treatment with Zn(O-Tf)2 induces a stereospecific cyclization via a SN2 process and exo mode selectivity giving oxepanes (II) and (IV) in good yields.

chemical structure image

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