Volume 29, Issue 1
Organoelement Compounds
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ChemInform Abstract: First Synthesis of Optically Pure Selenuranes and Stereoselective Alkaline Hydrolysis. Their Application to Asymmetric [2,3] Sigmatropic Rearrangement of Allylic Selenoxides.

N. KUROSE

N. KUROSE

Fac. Pharm. Sci., Toyama Med. Pharm. Univ., Sugitani, Toyama 930-01, Japan

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T. TAKAHASHI

T. TAKAHASHI

Fac. Pharm. Sci., Toyama Med. Pharm. Univ., Sugitani, Toyama 930-01, Japan

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T. KOIZUMI

T. KOIZUMI

Fac. Pharm. Sci., Toyama Med. Pharm. Univ., Sugitani, Toyama 930-01, Japan

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First published: 24 June 2010

Abstract

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ChemInform Abstract

The first chiral selenuranes (IV) are prepared utilizing the 2-exo-hydroxy-10-bornyl group as chiral moiety. Alkaline hydrolysis of (IV) proceeds with complete retention of configuration. Sigmatropic rearrangement of allylic selenoxides (IX) yields allylic alcohols (X) with moderate to good e.e.

chemical structure image

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