Next Article in Journal
Significance of Bioconvective and Thermally Dissipation Flow of Viscoelastic Nanoparticles with Activation Energy Features: Novel Biofuels Significance
Previous Article in Journal
Applying Educational Data Mining to Explore Students’ Learning Patterns in the Flipped Learning Approach for Coding Education
Previous Article in Special Issue
Asymmetric Electrophilic Reactions in Phosphorus Chemistry
Open AccessArticle

Preparation of Enantiomerically Enriched P-Stereogenic Dialkyl-Arylphosphine Oxides via Coordination Mediated Optical Resolution

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
*
Author to whom correspondence should be addressed.
Symmetry 2020, 12(2), 215; https://doi.org/10.3390/sym12020215
Received: 12 December 2019 / Revised: 10 January 2020 / Accepted: 14 January 2020 / Published: 2 February 2020
Optical resolution of several dialkyl-arylphosphine oxides was elaborated using the Ca2+ salt of (−)-O,O’-dibenzoyl-(2R,3R)-tartaric acid as the resolving agent. The conditions of crystallization and purification of the enantiomerically enriched phosphine oxides were optimized. Ethyl-phenyl-propylphosphine oxide and butyl-methyl-phenylphosphine oxide were prepared with an enantiomeric excess higher than 93%, whereas, three other dialkyl-arylphosphine oxides were obtained with an enantiomeric excess of 37–85%. It was also found that the sterically demanding alkyl chains hinder the formation of stable diastereomeric complexes, which consequently led to less efficient resolution procedures. View Full-Text
Keywords: dialkyl-arylphosphine oxide; P-stereogenic; optical resolution; enantiomeric separation dialkyl-arylphosphine oxide; P-stereogenic; optical resolution; enantiomeric separation
Show Figures

Graphical abstract

MDPI and ACS Style

Varga, B.; Bagi, P. Preparation of Enantiomerically Enriched P-Stereogenic Dialkyl-Arylphosphine Oxides via Coordination Mediated Optical Resolution. Symmetry 2020, 12, 215.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop