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

SYSNO ASEP	0345958
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Highly modular assembly of cationic helical scaffolds: rapid synthesis of diverse helquats via differential quaternization
Author(s)	Severa, Lukáš (UOCHB-X)_{RID, ORCID} Adriaenssens, Louis (UOCHB-X) Vávra, Jan (UOCHB-X)_RID Šaman, David (UOCHB-X)_{RID, ORCID} Císařová, I. (CZ) Fiedler, Pavel (UOCHB-X)_RID Teplý, Filip (UOCHB-X)_{RID, ORCID}
Number of authors	7
Source Title	Tetrahedron. - : Elsevier - ISSN 0040-4020 Roč. 66, č. 19 (2010), s. 3537-3552
Number of pages	16 s.
Language	eng - English
Country	GB - United Kingdom
Keywords	helquat ; helicene-viologen hybrid ; [2+2+2] cycloaddition ; extended diquat ; N-heteroaromatic cation
Subject RIV	CC - Organic Chemistry
R&D Projects	GA203/09/0705 GA ČR - Czech Science Foundation (CSF)
	GA203/09/1614 GA ČR - Czech Science Foundation (CSF)
CEZ	AV0Z40550506 - UOCHB-X (2005-2011)
UT WOS	000277967400020
DOI	10.1016/j.tet.2010.03.007
Annotation	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.
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434
Year of Publishing	2011

Number of the records: 1