Stereospecific synthesis of amphetamines
نویسندگان
چکیده
Regioselective addition of aryl lithium to commercially available (S)-(+)-propylene oxide provides the corresponding (S)-aryl-2-propanol. The (R)-amphetamine is obtained by conversion of the alcohol to the tosylate followed by azide displacement and hydrogenation. Mitsunobu conversion of the alcohol to the (R)-bromide followed by azide displacement and hydrogenation affords the (S)-amphetamine. © 2003 Elsevier Ltd. All rights reserved. approach is demonstrated by the use of this reaction sequence to prepare (R)-(−)-2,5-dimethoxy-4-methyl
منابع مشابه
Cyclodextrins in Asymmetric and Stereospecific Synthesis
Since their discovery, cyclodextrins have widely been used as green and easily available alternatives to promoters or catalysts of different chemical reactions in water. This review covers the research and application of cyclodextrins and their derivatives in asymmetric and stereospecific syntheses, with their division into three main groups: (1) cyclodextrins promoting asymmetric and stereospe...
متن کاملThe abused drug MDMA (Ecstasy) induces programmed death of human serotonergic cells.
The widely abused amphetamine analog 3,4-methylenedioxymethamphetamine (MDMA, also called "ecstasy") induces hallucination and psychostimulation, as well as long-term neuropsychiatric behaviors such as panic and psychosis. In rodents and monkeys, MDMA is cytotoxic to serotonergic neurons, but this is less clear with humans. Herein, MDMA was cytotoxic to human serotonergic JAR cells; it altered ...
متن کاملRecent advances in the polymerization of butadiene over the last decade
The stereospecific polymerization of conjugated dienes began in 1954 with the first catalysts obtained by combining TiCl4 or TiCl3 with aluminum-alkyls, i.e. the catalytic systems previously employed for ethylene and propylene polymerizations. Subsequently, many other catalytic systems were obtained and examined by a combination of transition metal or lanthanide compounds with appropriate alkyl...
متن کاملStereospecific Synthesis of Carbanucleotides Designed for Antisense Methodology
A short stereospecific synthesis of the carbocyclic 2 -deoxynucleoside analogues 36 and 37 (Schemes 2 and 5) and 45 and 46 (Schemes 2 and 6) starting from optically active 8,9,10-trinorborn-5-en-2-one (1) is described. As two functional groups capable to react with each other are present in the same molecule of the synthetic carbanucleosides, the latter can form polymers similar to oligonucleot...
متن کاملConfigurationally stable, enantioenriched organometallic nucleophiles in stereospecific Pd-catalyzed cross-coupling reactions: an alternative approach to asymmetric synthesis
Several research groups have recently developed methods to employ configurationally stable, enantioenriched organometallic nucleophiles in stereospecific Pd-catalyzed cross-coupling reactions. By establishing the absolute configuration of a chiral alkyltin or alkylboron nucleophile prior to its use in cross-coupling reactions, new stereogenic centers may be rapidly and reliably generated with p...
متن کامل