TY - JOUR
T1 - Design of resolving reagents
T2 - p-substituted mandelic acids as resolving reagents for 1-arylalkylamines
AU - Kinbara, Kazushi
AU - Sakai, Kenichi
AU - Hashimoto, Yukihiko
AU - Nohira, Hiroyuki
AU - Saigo, Kazuhiko
N1 - Funding Information:
arylalkylamines, which could scaroely be resolved by (R)-I. Moreover, it is noteworthy that (S)-I 1 and (R)-12 have a high resolving ability even for 2, as does (R)-I. This result indicates that these resolving reagents can resolve 1-arylalkylamines, having somewhat shorter molecular length than their molecular length, as well as 1-arylalkylamines with similar molecular length. The precise reason for such correlation between the efficiency of resolution and the length of resolving reagents is not known at present, although our previous study indicated that hydrogen-bond networks, formed in less-soluble salts, played a significant role in the chiral discrimination of 1-arylethylamines. 5 In order to elucidate this correlation more clearly, crystallographic studies concerning both more-and less-soluble diastereomeric salts are now in progress. In summary, it was found thatp-substituted mandelic acids (S)-I 1 and (R)-I 2 were suitable resolving reagents for p-substituted 1-arylalkylamines while (R)-I was suitable for non-or o-substituted 1-arylalkylamines. These results suggest that when one chooses a suitable resolving reagent for a given racemate, the complementarity in size between the resolving reagent and the racemate should be taken into account. Acknowledgment. The present work was supported by Grants-in-Aid for Scientific Research ('Nos. 07555581, 06242101 and 06004310) from the Ministry of Education, Science, Sports and Culture of Japan. K. K. is grateful for a Research Fellowship of the Japan Society for the Promotion of Science for Young Scientists.
PY - 1996/6
Y1 - 1996/6
N2 - The resolution of 1-arylalkylamines 2-10 by mandelic acid 1 was studied. It was found that a substituent, which elongated the molecular length of the amines, diminished the resolution efficiency. On the basis of these results, (S)-p-methylmandelic acid (S)-11 and (R)-p-methoxymandelic acid (R)-12 were selected as new resolving reagents for the 1-arylalkylamines; these acids were found to have a higher resolving ability than (R)-1.
AB - The resolution of 1-arylalkylamines 2-10 by mandelic acid 1 was studied. It was found that a substituent, which elongated the molecular length of the amines, diminished the resolution efficiency. On the basis of these results, (S)-p-methylmandelic acid (S)-11 and (R)-p-methoxymandelic acid (R)-12 were selected as new resolving reagents for the 1-arylalkylamines; these acids were found to have a higher resolving ability than (R)-1.
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U2 - 10.1016/0957-4166(96)00175-9
DO - 10.1016/0957-4166(96)00175-9
M3 - Article
AN - SCOPUS:0029950959
VL - 7
SP - 1539
EP - 1542
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 6
ER -