Phenyl ether 3-Phenylethylamine

L-Pkenylalanine, reaction with phthalic anhydride to yield N-phthalyl-L-phenylalanine, 40,82 Phenyl terf-BUTYL ether, 41, 91 a-Phenylethylamine, N-chlorination of, 41,82... 

An approach to the preparation of asymmetrically 1,2-disubstituted 1,2-diamines has been reported the zinc-copper-promoted reductive coupling of two different N-(4-substituted)phenyl aromatic imines, one bearing a 4-methoxy and the other a 4-chloro substituent, in the presence of either boron trifluoride or methyltrichlorosilane, gave a mixture of the three possible 1,2-diamines, where the mixed one predominated [31 ]. Low degrees of asymmetric induction were observed using 1-phenylethylamine, phenylglycinol and its 0-methyl ether, and several a-amino acid esters as the chiral auxiharies meanwhile the homocoupling process was not avoided (M.Shimizu, personal communication). 

ABSTRACT. The chiral recognition properties of chiral 18-crown-6 ethers with phenyl, l naphthoxymethyl, l naphthylmethyl, or 2,3,5,6-tetra-methylphenylmethyl substituents for a-phenylglycine methyl ester and 1-phenylethylamine perchlorate were investigated by a standard extraction procedure. The chiral recognition factor of 1-naphthoxymethyl substi-tuted crown ether is 2.0 for the former salt but near 1.0 for the latter, whereas that of the other crown ethers is not so dependent on the structure of salts, which indicates the importance of the mutual relation of the structure of host and guest molecules. 

In the present paper, we report the synthesis of chiral 18-crown-6 ethers with aromatic substituents of various rigidity and bulkiness, and the effects of substituents on their chiral recognition properties for 1-phenylethylamine and a-phenyl glycine methyl ester perchlorate. ... 

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