Tetrahedron: Asymmetry

Asymmetric Diels–Alder addition of cyclopentadiene to chiral naphthoquinones

MA Brimble, JF McEwan, P Turner

Index: Brimble, Margaret A.; McEwan, John F.; Turner, Peter Tetrahedron Asymmetry, 1998 , vol. 9, # 7 p. 1239 - 1255

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Citation Number: 18

Abstract

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 ...