Diels-Alder reaction—IX
1970; Elsevier BV; Volume: 26; Issue: 5 Linguagem: Inglês
10.1016/s0040-4020(01)92973-4
ISSN1464-5416
AutoresKen’ichi Takeda, Sanji Hagishita, Michi Sugiura, Keizo Kitahonoki, I. Ban, Shiori Miyazaki, Koichi Kuriyama,
Tópico(s)Molecular spectroscopy and chirality
ResumoAbstract The Diels-Alder reaction of 1,7-, 2,7-, 2,6-, 1,6-dihydroxynaphthalene and 6-bromo-2-naphthol with maleic anhydride was investigated. All of these 2-naphthol derivatives gave exo- and endo-adducts (II and III) except for the bromo-naphthol, from which only endo-adduct was obtained. The assignment of exo or endo configuration was based on lactone formation on NaBH4 reduction possible only from the exo isomer, comparison of NMR spectra and in some cases dipole moment measurements. The exo/endo ratios of the formed adducts vary over a wide range. Revolution of methoxy-trans-dicarboxylic acid VIII and IX was accomplished via the cinchonidine salts. The absolute configratuion of the resolved active compounds was determined by applying the octant rule.
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