Asymmetric Hydrocyanation of a Range of Aromatic and Aliphatic Aldehydes

Barry R. Matthews, W. Roy Jackson, Gamini S. Jayatilake, Colin Wilshire, Howard A. Jacobs

Research output: Contribution to journalArticleResearchpeer-review

72 Citations (Scopus)

Abstract

A range of aryl, alkyl and heterocyclic aldehydes have been treated with hydrogen cyanide in the presence of the ‘Inoue’ catalyst, (R, R)- or (S, S)-cyclo[phenylalanylhistidyl]. Most aryl aldehydes with electron-donating substituents in the m- or p-positions give high enantiomeric excess (e.e.) values (=80%) but aryl aldehydes with strong electron-withdrawing substituents gave moderate e.e. values (=50%). These moderate values are believed to be due to partial racemization of the product cyanohydrins in the presence of the mildly basic catalyst. In contrast to the reactions of aryl aldehydes, reactions of alkyl aldehydes and of ketones gave low e.e. values (=30%) and an explanation is proposed.

Original languageEnglish
Pages (from-to)1697-1709
Number of pages13
JournalAustralian Journal of Chemistry
Volume41
Issue number11
DOIs
Publication statusPublished - 1 Jan 1988

Cite this

Matthews, B. R., Roy Jackson, W., Jayatilake, G. S., Wilshire, C., & Jacobs, H. A. (1988). Asymmetric Hydrocyanation of a Range of Aromatic and Aliphatic Aldehydes. Australian Journal of Chemistry, 41(11), 1697-1709. https://doi.org/10.1071/CH9881697
Matthews, Barry R. ; Roy Jackson, W. ; Jayatilake, Gamini S. ; Wilshire, Colin ; Jacobs, Howard A. / Asymmetric Hydrocyanation of a Range of Aromatic and Aliphatic Aldehydes. In: Australian Journal of Chemistry. 1988 ; Vol. 41, No. 11. pp. 1697-1709.
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Matthews, BR, Roy Jackson, W, Jayatilake, GS, Wilshire, C & Jacobs, HA 1988, 'Asymmetric Hydrocyanation of a Range of Aromatic and Aliphatic Aldehydes', Australian Journal of Chemistry, vol. 41, no. 11, pp. 1697-1709. https://doi.org/10.1071/CH9881697

Asymmetric Hydrocyanation of a Range of Aromatic and Aliphatic Aldehydes. / Matthews, Barry R.; Roy Jackson, W.; Jayatilake, Gamini S.; Wilshire, Colin; Jacobs, Howard A.

In: Australian Journal of Chemistry, Vol. 41, No. 11, 01.01.1988, p. 1697-1709.

Research output: Contribution to journalArticleResearchpeer-review

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Matthews BR, Roy Jackson W, Jayatilake GS, Wilshire C, Jacobs HA. Asymmetric Hydrocyanation of a Range of Aromatic and Aliphatic Aldehydes. Australian Journal of Chemistry. 1988 Jan 1;41(11):1697-1709. https://doi.org/10.1071/CH9881697