ISSN:
0009-2940
Keywords:
(R)1-2-(Sulfonyloxy)nitriles, synthesis of, reaction with alkali acetates
;
(S)1-Cyanohydrin acetates, synthesis of
;
Nitriles
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Enzyme-Catalyzed Reactions, 15[1]. - Preparation of (R)1-2-(Sulfonyloxy)nitriles and Their Reactions with Acetates - Inversion of the Configuration of Optically Active Cyanohydrins2-(Sulfonyloxy)nitriles (R)-6, 7, 8 are obtained in high optical purity from the respective cyanohydrins (R)-2 by sulfonylation with methanesulfonyl chloride (3), toluenesulfonyl chloride (4), and trifluoromethanesulfonic anhydride (5), respectively. In contrast to the aliphatic (sulfonyloxy)nitriles (R)-6, 7, 8a - e, the benzylic-type mandelic acid derivatives (R)-7,8í are unstable at higher temperature. The 2-(sulfonyloxy)nitriles (R)1- 6, 7, 8a - e react at room temperature with alkali acetates in a typical SN2 manner to give the cyanohydrin acetates (S)-9 in high optical purity. Under these reaction conditions, however, the mandelic-type compounds (R)-7, 8í partly racemize and decompose. By hydrolysis of the acetates (S)-9, (S)1-cyanohydrins (S)-2 of aliphatic aldehydes are easily available.
Additional Material:
10 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260332
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