Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives
Available α-amino acids undergo arylation at their α position in an enantioselective manner on treatment with base of N′-aryl urea derivatives ligated to pseudoephedrine as a chiral auxiliary. In situ silylation and enolization induces diastereoselective migration of the N′-aryl group to the α position of the amino acid, followed by ring closure to a hydantoin with concomitant explulsion of the recyclable auxiliary. The hydrolysis of the hydantoin products provides derivatives of quaternary amino acids. The arylation avoids the use of heavy-metal additives, and is successful with a range of amino acids and with aryl rings of varying electronic character.
Atkinson, Rachel C.,Fernández-Nieto, Fernando,Mas Rosell?, Josep,Clayden, Jonathan
supporting information
p. 8961 - 8965
(2015/08/03)
Chromatographic Resolutions of Racemates, XI. Comparison of Optically Active Polyamides and Cellulose Triacetate
On optically active polyacrylic and polymethacrylic amides (1a-e) as well as on microcrystalline cellulose triacetate (2), numerous racemates including drugs are separated at least partially, the amide 4f completely on cellulose triacetate.By repeated chromatography on the polyamide 1a, (+)- and (-)-mandelic acid (4a) and (+)-hexobarbital (9d) also were obtained optically pure.
Racemic and Optically Active Hydantoins from Disubstituted Cyanoacetic Acids
Starting from the chiral disubstituted cyanoacetic acids 1 the racemates and some enantiomers of the 5,5-disubstituted hydantoins 6 and of the 3-methylhydantoins 7 are synthesized via the isocyanates 3.Their absolute configurations are determined.
Knabe, Joachim,Wunn, Wolfgang
p. 538 - 543
(2007/10/02)
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