Kinetic Resolution of Sulphoxides by Chiral Poly(N-Alkyliminoalanes)

DOI: 10.1039/P19810000113

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 113 - 118 (1981)

Update date:2022-07-29

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Authors:

Annunziata, Rita

Borgogno, Guido

Montanari, Fernando

Quici, Silvio

Cucinella, Salvatore

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Article abstract of DOI:10.1039/P19810000113

Kinetic resolution of racemic sulphoxides by chiral poly (PIA-PHETs) from (+) - or (-)-1-phenylethylamine is described.For p-tolyl mesityl sulphoxide in the temperature range between -25 and 85 deg C, optical yields increase with temperature to an upper limit of between 55 and 70 deg C, with enantiomeric enrichments up to 75percent.It is shown that, among the three molecular species of PIA-PHET (closed-cage tetramer, closed-cage hexamer and open-cage tetramer), only the last is chemically active and capable of chiral recognition.Reactions follow second-order kinetics (first-order in sulphoxide, first-order in open PIA-PHET tetramer).The particular molecular structure of the latter probably accounts for the high degree of chiral recognition at high temperature.

Full text of DOI:10.1039/P19810000113

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