Asymmetric Diels-Alder Addition of Cyclopentadiene to Chiral Naphthoquinones

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Title

Asymmetric Diels-Alder Addition of Cyclopentadiene to Chiral Naphthoquinones

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The University of Auckland Library

Collection

ResearchSpace@Auckland

Description

Diels-Alder reactions of 1,4-naphthoquinones bearing a chiral auxiliary at C-2, with cyclopentadiene under Lewis acid conditions afforded the corresponding Diels-Alder. adducts. High levels of diastereomeric excess were obtained using (R)-pantolactone, (S)-N-methyl-2-hydroxysuccinimide and trans-2-phenylcyclohexanol as auxiliaries. Moderate asymmetric induction was achieved using Oppolzer's camphorsultam and (R)-(+)-4-benzyl-2-oxazolidinone as auxiliaries. X-Ray crystallographic analysis of t...

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Format

Research paper

Research format

Journal article

Date created

1998

Creator

Brimble, Margaret / Mcewan, JF / Murray, Pamela

URL

http://hdl.handle.net/2292/8076

Related subjects

LEWIS ACID / CYCLOADDITIONS / INDUCTION / REAGENTS / MODEL

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