Related Experiment Video
Updated: Aug 12, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Effective resolution of chiral 1,1':5',1"-ternaphthalene-2,2',6',2"-tetrol through camphorsulfonylation,
1Faculty of Science, Himeji Institute of Technology, Kanaji, Hyogo, Japan. sugimura@sci.himeji-tech.ac.jp
Abstract:
Optical resolution of the title compound, TERNOL (1), having bis-bidentate sites of axial chiralities was succesful. A racemic mixture of 1 was converted to the tetracamphorsulfonate 2 in high yield, and a single recrystallization of 2 under kinetic conditions effectively separated the diastereomers. The crystal part obtained in 44% yield consisted of (S,S)-2 of 96% diastereomer excess (de), and the solution part (50% yield) contained (R,R)-2 of 96% de. An additional recrystallization of the each part resulted in diastereomerically pure 2 in high yield. Hydride reduction of the ketones in the camphorsulfonyl groups of 2 caused smooth intramolecular transesterification, and enantiomerically pure (R,R)-1 and (S,S)-1 were obtained in good yields.
Related Concept Videos
Prochirality
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Preparation and Reactions of Sulfides
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Woodward–Hoffmann Selection Rules and Microscopic Reversibility
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

