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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 75, 1993 - Issue 1-4
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SECTION I: PHOSPHORUS IN ORGANIC SYNTHESES

Inversion of the Configuration of Cyanohydrins by a Mitsunobu Esterification Reaction

E. G.J.C. Warmerdam Department of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300, RA, Leiden, The Netherlands
,
J. Brussee Department of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300, RA, Leiden, The Netherlands
,
C. G. Kruse Solvay Duphar B.V., P.O. Box 900, 1380, AA, Weesp, The Netherlands
&
A. van der Gen Department of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300, RA, Leiden, The Netherlands
Pages 3-6 | Published online: 23 Sep 2006
 
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Abstract

Optically active (R)-cyanohydrins have been transformed into cyanohydrin esters of opposite configuration under Mitsunobu conditions and subsequently solvolyzed to (S)-cyanohydrins in high chemical and optical yield. The method works well for allylic and benzylic cyanohydrins. Cyanohydrins containing strongly electron donating substituents gave extensive racemization. Saturated aliphatic cyanohydrins afforded esters in which the original configuration is retained. These results are discussed in terms of the mechanism of the Mitsunobu reaction.

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