R and S isomer of Trogers base

These hosts were used to study inclusion complexation with aromatic guests in aqueous solution.23 The differences in binding between the phenethylamines and the benzylamines are shown in Table 1. Host 13 and 14 bound aromatic guests better than host 15 and 16. It is possible that the ammonium groups of the benzyl amine hosts are directed into the cavity this reduces its hydrophobicity and results in a low binding constant. There was also a strong 

It was converted to the phthalimide via a Mitsunobu reaction, reduced to the amine, and the amine was coupled with / -nitrophenylacetic acid to give the precursor to the macrocycle. Macrocylization was done via Troger s base formation using Johnson s method, which resulted in two isomers of the amide macrocycle. These were separated and reduced to give the cyclophane host. This was the first time two diastereomers were observed in these syntheses and the separation of these diastereomers was very difficult. 

5 % overall yield of both isomers from the dialcohol 

It was necessary at this stage to develop a reliable synthesis to host 17. Dr. Muneharu Miyake developed a new route to 17. During this time I joined the group and was assigned the 

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