Author Topic: Stereoselective (S)-MDA synth via the Cyanohydrin  (Read 5241 times)

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Stereoselective (S)-MDA synth via the Cyanohydrin
« on: March 26, 2003, 02:24:00 AM »
Stereoselective Synthesis of (S)-3,4-Methylenedioxyamphetamines from (R)-Cyanohydrins

Chem. Eur. J. 3(8),1370-1371 (1997)


A lot of interesting chemistry, including grignard alkylation of Piperonal cyanohydrin to form the corresponding phenylpropanolamine. Note that the intermediate amide 6 is of the same type as the one gotten from the reaction of norpseudoephedrine with potassium cyanate, and according to this ref it can be reduced to the amphetamine with 1 atm H2.

If you are specifically interested in the generation of chiral cyanohydrins, the literature is filled to the brim with such procedures not using as exotic reagents like the enzyme used in this article.


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Optically Active Cyanohydrins Using Almond Meal
« Reply #1 on: January 15, 2004, 05:19:00 AM »
Synthesis of Optically Active Cyanohydrins Using Almond Meal
P. Zandbergen, J. van der Linden, J. Brussee and A. van der Gen.

Synth. Commun. 21(12-13), 1387-1391 (1991)


Asymmetric hydrocyanation of aldehydes was accomplished using almond meal, containing the enzyme oxynitrilase. Optically active cyanohydrins with high levels of enantiomeric purity were obtained following a simple procedure.

Other use for these chiral cyanohydrins:

Post 403276

(java: "Synth of  Ephedrine from protected Cyanohydrins", Methods Discourse)