ISSN:
0947-6539
Keywords:
amphetamines
;
cyanohydrins
;
enzyme catalysis
;
hydrogenations
;
oxazolidinones
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A stereoselective synthesis of (S)-3,4-methylenedioxyamphetamines (S)-7, which are highly interesting as psychoactive compounds, is described. Starting from readily available (R)-cyanohydrins (R)-2 the 2-amino-1-aryl alcohols (1R,2S)-4 were obtained with high diastereoselectivity by addition of Grignard reagents to the O-protected cyanohydrins (R)-3, transimination of the addition products A with primary amines, and hydrogenation of the imino intermediates B with NaBH4. For the hydrogenation of the benzylic hydroxyl group in the 1,2-amino alcohols (1R,2S)-4 a new, very efficient method was developed. The optically pure amphetamines (S)-7 were obtained under very mild conditions by catalytic hydrogenation of the oxazolidinones (4S,5R)-6, which were readily available by phosgenation of the amino alcohols (1R,2S)-4.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19970030825
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