NDLI: The Brønsted Acid Catalyzed, Enantioselective Vinylogous Mannich Reaction

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The Brønsted Acid Catalyzed, Enantioselective Vinylogous Mannich Reaction

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Birkemeyer, Claudia Lang, Matthias Schneider, Christoph Abels, Falko Sickert, Marcel Sieler, Joachim
Description	Author Affiliation: Sickert M ( Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany.)
Abstract	The first catalytic, enantioselective vinylogous Mannich reaction of acyclic silyl dienolates is reported. A second-generation 2,2′-dihydroxy-1,1′-binaphthyl (BINOL)-based phosphoric acid has been developed and further optimized as an enantioselective organocatalyst. Upon protonation of the imines, chiral contact ion pairs are generated in situ and attacked highly diastereoselectively by the nucleophile. γ-Substituted silyl dienolates that lead to more highly substituted Mannich products with a second stereogenic center in good diastereoselectivity have been employed in these reactions. The reaction path has been elucidated with NMR spectroscopy and mass spectrometry, which suggest that the protic reaction medium found to be optimal in these reactions serves to trap the cationic silicon species as silanol. A crystal structure of a phosphoric acid bound imine was obtained that provides insight into the binding mode and a rationale for the stereochemical course of the reaction.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	9
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-03-01
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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