Optical resolution of phosphinates and phosphine oxides by complex formation with optically active 2,2'-dihydroxy-1,1'-binaphthyl and crystallographic study of two diastereomeric complexes with methyl methylphenylphosphinate

1988 ◽  
Vol 53 (2) ◽  
pp. 308-312 ◽  
Author(s):  
Fumio Toda ◽  
Koji Mori ◽  
Zafra Stein ◽  
Israel Goldberg
Keyword(s):  
Complex Formation ◽  
Optical Resolution ◽  
Optically Active ◽  
Phosphine Oxides ◽  
Crystallographic Study ◽  
Diastereomeric Complexes

Optical resolution of amine N-oxide by diastereoisomeric complex formation with optically active host compound

1989 ◽  
Vol 30 (14) ◽  
pp. 1841-1844 ◽  
Author(s):  
Fumio Toda ◽  
Koji Mori ◽  
Zafra Stein ◽  
Israel Goldberg
Keyword(s):  
Complex Formation ◽  
Optical Resolution ◽  
Optically Active ◽  
Host Compound

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

Symmetry ◽  
2020 ◽  
Vol 12 (2) ◽  
pp. 215 ◽  
Author(s):  
Varga ◽  
Bagi
Keyword(s):  
Tartaric Acid ◽  
Enantiomeric Excess ◽  
Optical Resolution ◽  
Phosphine Oxides ◽  
Alkyl Chains ◽  
Sterically Demanding ◽  
Diastereomeric Complexes ◽  
Phenylphosphine Oxide

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.

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