Tetrahedron: Asymmetry

Asymmetric Diels–Alder addition of cyclopentadiene to chiral naphthoquinones

MA Brimble, JF McEwan, P Turner

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

全文：HTML全文

被引用次数: 18

摘要

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 ...