227315-20-0Relevant articles and documents
Influence of the metal and chiral diamine on metal(II)salen catalysed, asymmetric synthesis of α-methyl α-amino acids
Belokon, Yuri N.,Fuentes, Jose,North, Michael,Steed, Jonathan W.
, p. 3191 - 3204 (2007/10/03)
The influence of the metal ion and chiral diamine used to form a metal(salen) complex on the catalytic activity of the complex in the asymmetric benzylation of an alanine enolate was investigated. Only metal ions which could form square-planar complexes g
Asymmetric Synthesis of 1,2-Diamino-4,5-dimethylcyclohexanes by Zirconium-Catalyzed and -Promoted Reductive Cyclization Reactions
Grepioni, Fabrizia,Grilli, Stefano,Martelli, Gianluca,Savoia, Diego
, p. 3679 - 3683 (2007/10/03)
The asymmetric synthesis of 1,2-diamino-4,5-dimethylcyclohexanes was achieved by the zirconium-catalyzed and -promoted reductive cyclization of N,N′-di[(S)-1-phenylethyl]-4CR),5(R)-diamino-1,7-octadiene. The reaction of the diene with 5 equiv of butylmagnesium chloride and 0.1 mol % of bis(cyclopentadienyl)zirconium dichloride in diethyl ether at 0-20°C gave mainly the 1(R),2(R)-diamino-4(S),5(S)-dimethylcyclohexane derivative having C2 symmetry, but the reaction with 4 equiv of dibutylzirconocene in tetrahydrofuran at -78 to -50°C gave prevalently the diastereomer with the 4(R),5(S) configuration. By reductive cleavage of the auxiliary, followed by sulfonylation reaction, 1(R),2(R)-di(4-toluenesulfonyl)amino)-4(S),5(S)-dimethylcyclohexane was prepared.