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ChemInform Abstract: Asymmetric Diels—Alder Addition of Cyclopentadiene to Chiral Naphthoquinones.

✍ Scribed by M. A. BRIMBLE; J. F. MCEWAN; P. TURNER

Publisher
John Wiley and Sons
Year
2010
Weight
39 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Asymmetric Diels-Alder Addition of Cyclopentadiene to Chiral Naphthoquinones.

-The Lewis acid mediated Diels-Alder reaction of naphthoquinones bearing various chiral auxiliaries with cyclopentadiene is investigated. High levels of diastereoselectivity are observed using N-methyl-2-hydroxysuccinimide and trans-2-phenylcyclohexanol as auxiliaries. The cycloadducts can be transformed into cyclopentannulated pyranonaphthoquinones, e.g. (XIII), useful precursors for the preparation of pyranonaphthoquinone an-

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