208335-56-2Relevant academic research and scientific papers
Asymmetric Diels-Alder addition of cyclopentadiene to chiral naphthoquinones
Brimble, Margaret A.,McEwan, John F.,Turner, Peter
, p. 1239 - 1255 (2007/10/03)
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 the pantolactone adduct enabled determination of the stereochemistry of all adducts obtained.
