Configurations of cycloadducts formed in asymmetric intramolecular Diels-Alder reactions

Breu, Josef and Butz, Thomas and Range, Klaus-Jürgen and Sauer, Jürgen (1997) Configurations of cycloadducts formed in asymmetric intramolecular Diels-Alder reactions. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 53 (4). pp. 515-517. ISSN 0108-2701, 1600-5759

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Abstract

Intramolecular cycloaddition reactions of two furfuryl fumarates yield, after crystallization, pure diastereomers of oxabicyclo[2.2.1]heptene derivatives which are versatile starting points for the total synthesis of natural products. The crystal structures of the adducts, menthyl (3aS,6R,7R,7aR)-1,3,3a,6,7,7a-hexahydro-3,3-dimethyl-1-oxo-3a,6- epoxyisobenzofuran-7-carboxylate, C21H30O5, and methyl syn-3-tert-butyl-1,3,3a,6,7,7a-hexahydro-1- oxo-3a,6-epoxyisobenzofuran-7-carboxylat, C14H18O5, establish the configuration at the chiral centers and provide insights into the factors controlling the diastereomeric differentiation.

Item Type: Article
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Anorganische Chemie > Alumni or Retired Professors > Prof. Dr. Klaus-Jürgen Range
Chemistry and Pharmacy > Institut für Organische Chemie
Depositing User: Dr. Gernot Deinzer
Date Deposited: 09 May 2023 07:51
Last Modified: 09 May 2023 07:51
URI: https://pred.uni-regensburg.de/id/eprint/50876

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