4.6 Article

C-1-Symmetric Aminosulfoximines in Copper-Catalyzed Asymmetric Vinylogous Mukaiyama Aldol Reactions

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 15, Pages 4577-4587

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200903077

Keywords

aldol reaction; asymmetric catalysis; copper; Mukaiyama reaction; sulfoximine

Funding

  1. Fonds der Chemischen Industrie

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Vinylogous Mukaiyama-type aldol reactions have been catalyzed by a combination of Cu(OTf)(2), and readily available C-1-symmetric aminosulfoximines. After a fine-tuning of the reaction conditions and an optimization of the modularly assembled ligand structure. high stereoselectivities and excellent yields have been achieved in catalyzed reactions involving various electrophile/nucleophile combinations. The relative and absolute configurations of two products were assigned by X-ray single crystal structure analysis and a comparison of calculated and experimental CD spectra.

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