Journal article

Publication year: 2015

Pages: 13106-13109

Journal: Angewandte Chemie International Edition

Volume number: 54

Issue number: 44

DOI Link: https://doi.org/10.1002/anie.201505349

Publisher: Wiley

Abstract: 

The determination of the absolute configuration of chiral molecules is
at the heart of asymmetric synthesis. Here we probe the spectroscopic
limits for chiral discrimination with NMR spectroscopy in chiral aligned
media and with vibrational circular dichroism spectroscopy of the
sixfold‐deuterated chiral neopentane. The study of this compound
presents formidable challenges since its stereogenicity is only due to
small mass differences. For this purpose, we selectively prepared both
enantiomers of ²H₆‐1 through a concise
synthesis utilizing multifunctional intermediates. While NMR
spectroscopy in chiral aligned media could be used to characterize the
precursors to ²H₆‐1, the final assignment could only be accomplished with VCD spectroscopy, despite the fleetingly small dichroic properties of 1. Both enantiomers were assigned by matching the VCD spectra with those computed with density functional theory.

Harvard Citation style: Masarwa, A., Gerbig, D., Oskar, L., Loewenstein, A., Reisenauer, H., Lesot, P., et al. (2015) Synthesis and Stereochemical Assignment of Crypto‐Optically Active 2H6‐Neopentane, Angewandte Chemie International Edition, 54(44), pp. 13106-13109. https://doi.org/10.1002/anie.201505349

APA Citation style: Masarwa, A., Gerbig, D., Oskar, L., Loewenstein, A., Reisenauer, H., Lesot, P., Schreiner, P., & Marek, I. (2015). Synthesis and Stereochemical Assignment of Crypto‐Optically Active 2H6‐Neopentane. Angewandte Chemie International Edition. 54(44), 13106-13109. https://doi.org/10.1002/anie.201505349