Dynamic Kinetic Resolution of Phosphinic Acid Derivatives via Nucleophilic­ Substitution at Phosphorus Center

Dorota Strzelecka; Olga Bąk; Piotr Borowski; Marek Stankevič

doi:10.1055/s-0037-1609947

Synthesis, Table of Contents

Synthesis 2018; 50(24): 4922-4932
DOI: 10.1055/s-0037-1609947

paper

Dynamic Kinetic Resolution of Phosphinic Acid Derivatives via Nucleophilic Substitution at Phosphorus Center

Dorota Strzelecka

^aDepartment of Organic Chemistry, Faculty of Chemistry, Marie Curie-Sklodowska University in Lublin, 33 Gliniana St., 20-614 Lublin, Poland Email: marek.stankevic@poczta.umcs.lublin.pl

,

Olga Bąk

^bDepartment of Chromatographic Methods, Faculty of Chemistry, Marie Curie-Sklodowska University in Lublin, 3 Marie Curie-Sklodowska Sq., 20-031 Lublin, Poland Email: piotr.borowski@poczta.umcs.lublin.pl

,

Piotr Borowski*

^bDepartment of Chromatographic Methods, Faculty of Chemistry, Marie Curie-Sklodowska University in Lublin, 3 Marie Curie-Sklodowska Sq., 20-031 Lublin, Poland Email: piotr.borowski@poczta.umcs.lublin.pl

,

Marek Stankevič *

^aDepartment of Organic Chemistry, Faculty of Chemistry, Marie Curie-Sklodowska University in Lublin, 33 Gliniana St., 20-614 Lublin, Poland Email: marek.stankevic@poczta.umcs.lublin.pl

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Abstract

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Abstract

Reaction of racemic phosphinic acid derivatives with chiral alcohols proceeds with predominant formation of one diastereomer. The highest level of enrichment has been obtained for transesterfication of racemic methyl benzylphenylphosphinate (64% de). The outcome of the reaction depends on both the structure of chiral alcohol and the starting organophosphorus compound. The results strongly suggest that the nature of the observed phenomena is not a classical equilibration of intermediates found in dynamic kinetic resolution process but is a result of a different reactivity of both enantiomers of racemic substrate towards the same chiral nucleophile.

Key words

phosphinic acid derivatives - transesterification - dynamic kinetic resolution - Berry pseudorotation - stereochemistry

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References

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Supplementary Material

Supporting Information

Dynamic Kinetic Resolution of Phosphinic Acid Derivatives via Nucleophilic­ Substitution at Phosphorus Center

Dynamic Kinetic Resolution of Phosphinic Acid Derivatives via Nucleophilic Substitution at Phosphorus Center