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Chirality via Upper and Lower Rim Substitution Patterns

A more subtle way to generate a chiral calixarene is to create dissymmetry or asymmetry within the molecule itself One of the means for doing this with a calix[4]arene is to establish a substitution pattern of AABC or ABCD on the upper or lower rim, producing a compound that is inherently chiral in all possible conformations. Tabulations of the cone, partial cone, 1,2-alternate, and [Pg.136]

Arimura, T. Edamitsu, S. Shinkai, S. Manabe, O. Muramatsu, T. Tashiro, T. Chem. Lett. 1987, [Pg.136]

Bottino, A. Geraci, C. Piattelli, M. Tetrahedron Asymmetry 1996, 7, 17. [Pg.136]

Iwamoto, K. Yanagi, A. Arimura, T. Matsuda, T. Shinkai, S. Chem. Lett. 1990, 1901. [Pg.137]

252e AABB CH,CO,MeCH,CO,MeCH,CO,H CH,CO,H SO,Ar S02Ar S02Ar S02Ar 1,2-alt 272 [Pg.138]


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Chiral pattern

Lower upper

Substitution patterns

Upper rim

Upper rim substitution

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