4-Methoxy-phenylamine

SYNS o-AMINOANISOLE 2-AMINOANISOLE 1-AMINO-2-METHOXYBENZENE 2-ANISIDINE o-ANISYLAMINE BENZENAMINE, 2-METHOXY-(9CI) 2-METHOXY-l-AMINOBENZENE o-METHOXYANILINE 2-METHOXYANILINE 2-METHOXYBENZENAMINE o-METHOXY-PHENYLAMINE... 

SYNS p-AMINOANISOLE 4-AMINOANISOLE 1-AMINO-4-METHOXYBENZENE 4-ANISIDINE p-ANISYLAMINE p-METHOXYANIUNE 4-METHOXYANILINE 4-METHOXYBENZENAMINE 4-METHOXYBENZENEAMINE p-METHOXY-PHENYLAMINE... 

Recently, Ueno et al used the chiral zirconium catalyst 7.4.4 for asymmetric induction. Thus, reaction of imine 7.4.5 and silyl enol ether 7.4.6 in the presence of 10 mol% S-IAA gave the desired phenyl isoserine derivative 7.4.7 in 94% ee and 95% yield. The a-hydroxy-phenylamine which was required for the catalytic asymmetric induction was then cleaved oxidatively using CAN after being converted to an a-methoxy-phenylamine derivative. Aqueous hydrolysis of the resulting aminoester 7.4.8 yielded the amino acid quantitatively, which was benzoylated to give the taxol side chain (269). 

Condensation of l-bromo-2-methoxy-4-methyl benzene (64) with 5,6-dimethoxyaniline acetate (65) in pyridine in the presence of Cu and K2CO3 and subsequent hydrolysis with 20% KOH furnished the di-phenylamine derivative (66) which on treatment with palladium acetate in DMF afforded murrayastine (13). Condensation of l-bromo-3-methoxy-4-methylbenzene (67) with the dimethyl acetal of 6-formyl-5-methoxyaniline acetate (68) furnished the diphenylamine derivative (69) which on hydrolysis and on subsequent cyclisation furnished murray-aline (14). 

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