☆ 4.6 Article

Synthesis of Tetrasubstituted Alkenes through a Palladium-Catalyzed Domino Carbopalladation/C-H-Activation Reaction

CHEMISTRY-A EUROPEAN JOURNAL (2012)

Journal

CHEMISTRY-A EUROPEAN JOURNAL

Volume 18, Issue 11, Pages 3286-3291

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/chem.201103209

Keywords

C?H activation; domino reactions; helical structures; molecular switches; palladium

Categories

Chemistry, Multidisciplinary

Funding

Deutsche Forschungsgemeinschaft
Center for Material Crystallography
Fonds der Chemischen Industrie

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Abstract

Helical tetrasubstituted alkenes (7) were obtained in a highly efficient way through a palladium-catalyzed domino-carbopalladation/CH-activation reaction of propargylic alcohols 6 in good to excellent yields. Electron-withdrawing- and electron-donating substituents can be introduced onto the upper and lower aromatic rings. The substrates (6) for the domino process were synthesized by addition of the lithiated alkyne (20) to various aldehydes (19); moreover, the substrates were accessible enantioselectively (in 95?% ee) by reduction of the corresponding ketone using the Noyori procedure.

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