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Inversion of the configuration of cyanohydrins by a mitsunobu esterification reaction

✍ Scribed by Erwin G.J.C. Warmerdam; Johannes Brussee; Chris G. Kruse; Arne van der Gen

Book ID
104203866
Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
569 KB
Volume
49
Category
Article
ISSN
0040-4020

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✦ Synopsis

optically active (R)-cyanohydrins have been transformed into cyanohydrin esters of opposite configuration under Mitsunobu conditions and subsequently solvolyxed to (S)-cyanohydrins in high chemical and optical yield. The method works well for allylic sod benxylic cyaaohydrins. Cyanohytis containing strongly electron doaaung substituents gave extensive racemuzktn. Saturated ahphatic cyanohydrins affonkd esters in which the original configmatum is retained. These results are discussed in terms of the mechanism of the Mitsunobu reaction.

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