Method of preparing optically active cyanohydrin derivatives

Details Method of preparing optically active cyanohydrin derivatives Method of preparing optically active cyanohydrin derivatives

1993-12-06

1996-02-20

Brust, Joseph Paul

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitriles

558398, 558399, 558406, 546330, 548531, 549 71, 549484, C07C25330, C07C25332

Patent

active

054930472

ABSTRACT:
The invention relates to a method of preparing an optically active cyanohydrin carboxylic acid ester from an optically active cyanohydrin of opposite configuration, wherein said starting cyanohydrin is converted with a carboxylic acid in the presence of a dialkyl azodicarboxylate and a triarylphosphine.
The invention also relates to a method of preparing an optically active cyanohydrin of opposite configuration by a subsequent solvolysis of the ester obtained under conservation of the configuration.

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J. Org. Chem., (1987), pp. 4978-4984, Teodozyj Kolasa et al., "Rections of .alpha.-Hydroxy Carbonyl Compounds with Azodicarboxylates and Triphenylphosphine: Synthesis of .alpha.-N-Hydroxy Amino Acid Derivatives".
Synthesis, (1981) pp. 1-28, Oyo Mitsunobu, "The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products".
Tetrahedron Letters, vol. 30, No. 23, (1989), pp. 3057-3058, H. Waldmann.
Camp, et. al.; J. Org. Chem. (1989), 54, pp. 3049-3054.

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