Volume 24, Issue 32
Preparative Organic Chemistry
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ChemInform Abstract: Lewis Acid Mediated Cyclization of ortho-Allyl Substituted Homochiral Anthraquinone Dioxolanes.

R. C. CAMBIE

R. C. CAMBIE

Dep. Chem., Univ. Auckland, Private Bag, Auckland, N. Z.

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S. E. HOLROYD

S. E. HOLROYD

Dep. Chem., Univ. Auckland, Private Bag, Auckland, N. Z.

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P. S. RUTLEDGE

P. S. RUTLEDGE

Dep. Chem., Univ. Auckland, Private Bag, Auckland, N. Z.

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P. D. WOODGATE

P. D. WOODGATE

Dep. Chem., Univ. Auckland, Private Bag, Auckland, N. Z.

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First published: August 10, 1993

Abstract

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ChemInform Abstract

The cleavage and recyclization reaction of the 2-allyl-3-dioxolanyl- substituted anthraquinone derivatives (I) under the influence of SnCl4 or TiCl4 is investigated. Both Lewis acids favor the formation of the diastereomers (III). In this reaction, two stereocenters are generated simultaneously. Other by-products are described in the original paper.

chemical structure image

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