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π-Helicenes truncated to a minimum: access through a domino approach involving multiple carbopalladations and a
Bastian Milde1, Markus Leibeling, Martin Pawliczek
1Technische Universität Braunschweig, Institut für Organische Chemie, Hagenring 30, 38106 Braunschweig (Germany) http://www.werzlab.de.
Abstract:
A novel type of π-helicenes is reported, in which the π-system is truncated to an all-s-cis all-Z oligoene chain. A domino sequence was developed, consisting of up to four consecutive carbopalladation reactions and a terminal Stille cross-coupling, to generate these entities in one step from the respective linear oligoynes. Despite the minimal π-system, very high optical rotation values were encountered for the single enantiomers. X-ray crystallography confirmed their screw-shaped structure.
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