Highly modular assembly of cationic helical scaffolds: rapid synthesis of diverse helquats via differential quaternization

0345958 - ÚOCHB 2011 RIV GB eng J - Článek v odborném periodiku
Severa, Lukáš - Adriaenssens, Louis - Vávra, Jan - Šaman, David - Císařová, I. - Fiedler, Pavel - Teplý, Filip
Highly modular assembly of cationic helical scaffolds: rapid synthesis of diverse helquats via differential quaternization.
Tetrahedron. Roč. 66, č. 19 (2010), s. 3537-3552. ISSN 0040-4020. E-ISSN 1464-5416
Grant CEP: GA ČR GA203/09/0705; GA ČR GA203/09/1614
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: helquat * helicene-viologen hybrid * [2+2+2] cycloaddition * extended diquat * N-heteroaromatic cation
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 3.011, rok: 2010

A protocol for rapid and highly modular assembly of a diverse set of helquats is described. From a common bis-isoquinoline precursor, two successive distinct pyridine-type nitrogen quaternizations followed by rhodium-catalyzed [2+2+2] cycloaddition afford non-symmetric [7]helquats. This route allows for straightforward molecular editing of cationic helical skeletons as exemplified by the synthesis of 15 different [5]-, [6]-, and [7]helquats. The use of pyridine-type nitrogen as a functionalization handle makes the route exclusively skeleton-building and therefore markedly step economic.
Trvalý link: http://hdl.handle.net/11104/0187115