Journal article

Publication year: 2021

Pages: 113-117

Journal: Organic Letters

Volume number: 23

Issue number: 1

ISSN: 1523-7052

DOI Link: https://doi.org/10.1021/acs.orglett.0c03795

Publisher: American Chemical Society

Abstract: 

We report the synthesis and absolute configuration of monodeuterated cis-perhydroazulene (d₁-1), which is a rare example of an isotopically chiral hydrocarbon whose synthesis and stereochemical analysis are known to be particularly difficult. The synthesis features nickel-boride-catalyzed deuteration that allowed formation of the diastereomerically pure cis-fused bicyclic system in d₁-1. The vibrational circular dichroism results are in excellent agreement with the computed spectrum at ωB97XD/aug-cc-pVTZ, allowing unambiguous assignment of the absolute configuration of d₁-1.

Harvard Citation style: Saito, F., Gerbig, D., Becker, J. and Schreiner, P. (2021) Breaking the Symmetry of a Meso Compound by Isotopic Substitution: Synthesis and Stereochemical Assignment of Monodeuterated cis-Perhydroazulene, Organic Letters, 23(1), pp. 113-117. https://doi.org/10.1021/acs.orglett.0c03795

APA Citation style: Saito, F., Gerbig, D., Becker, J., & Schreiner, P. (2021). Breaking the Symmetry of a Meso Compound by Isotopic Substitution: Synthesis and Stereochemical Assignment of Monodeuterated cis-Perhydroazulene. Organic Letters. 23(1), 113-117. https://doi.org/10.1021/acs.orglett.0c03795