Stereoselective Single Step Cyclization to Give Belt-Functionalized Pillar[6]arenes.
J Org Chem
; 89(3): 1397-1406, 2024 Feb 02.
Article
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| MEDLINE
| ID: mdl-38214497
ABSTRACT
Two macrocycles were synthesized through cyclization reactions of secondary benzylic alcohols, giving pillar[6]arenes with a methyl substituent at each belt position. These macrocycles form stereoselectively with only the rtctct isomer with alternating up and down orientations of the belt methyl groups definitively identified. Isolated yields were modest (7 and 9%), but the macrocycles are prepared in a single step from either a commercially available alcohol or a very readily prepared precursor. X-ray crystal structures of the macrocycles indicate they have a capsule-like structure, which is far from the conventional pillar shape. Density functional theory calculations reveal that the energy barrier required to obtain the pillar conformation is significantly higher for these belt-functionalized macrocycles than for conventional belt-unfunctionalized pillar[6]arenes.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2024
Tipo del documento:
Article
País de afiliación:
Australia
Pais de publicación:
Estados Unidos