Document Type

Article

Publication Date

6-29-2018

Publication Title

European Journal of Organic Chemistry

Volume

2018

Issue

33

Pages

4639-4645

Abstract

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.

Comments

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.

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