Attempted Resolution and Racemization of Beckmann‐Derived CTV‐Lactam and the Use of Chirabite‐AR® to Determine the Optical Purity of the Supramolecular Scaffold
European Journal of Organic Chemistry
Chirabite‐AR was employed to differentiate enantiomers of the axially chiral cyclotriveratrylene (CTV)‐derived macrocyclic lactam with baseline separation of most of the proton NMR resonances enabling enantiomeric purity determination of this supramolecular scaffold. Attachment of menthyloxy acetic acid as a chiral auxiliary to the CTV‐Beckmann derived lactam afforded diastereomers that were enriched to a ratio of 87:13, as confirmed by both 1H NMR and single‐crystal X‐ray diffraction. Basic hydrolysis of the enriched diastereomeric mixture proceeded with rapid bowl inversion to yield racemic CTV‐lactam as confirmed by Chirabite‐AR NMR analysis. Density functional theory (DFT) calculations (M06 2X/6‐31G*) were performed on the crown and saddle conformers of the CTV‐lactam.
Lutz Jr., Marlon R.; Ernst, Elizabeth; Zeller, Matthias; Dudzinski, Jacob; Thoresen, Peter; and Becker, Daniel P.. Attempted Resolution and Racemization of Beckmann‐Derived CTV‐Lactam and the Use of Chirabite‐AR® to Determine the Optical Purity of the Supramolecular Scaffold. European Journal of Organic Chemistry, 2018, 33: 4639-4645, 2018. Retrieved from Loyola eCommons, Chemistry: Faculty Publications and Other Works, http://dx.doi.org/10.1002/ejoc.201800788
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Author Posting. © WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2018. This article is posted here by permission of WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim for personal use, not for redistribution. The article was published in the European Journal of Organic Chemistry, 2018, https://doi.org/10.1002/ejoc.201800788.