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Asymmetric Organocatalytic Reactions of α,β-Unsaturated Cyclic Ketones

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Author(s): Renato Dalpozzo | Giuseppe Bartoli | Giorgio Bencivenni

Journal: Symmetry
ISSN 2073-8994

Volume: 3;
Issue: 1;
Start page: 84;
Date: 2011;
Original page

Keywords: α | β-unsaturated ketones | organocatalysis | iminium ion | Michael addition

ABSTRACT
The 1,4-conjugate addition of nucleophiles to α,β-unsaturated carbonyl compounds represents one fundamental bond-forming reaction in organic synthesis. The development of effective organocatalysts for the enantioselective conjugate addition of malonate, nitroalkane and other carbon and heteroatom nucleophiles to cycloenones constitutes an important research field and has been explored in recent years. At the same time, asymmetric Diels-Alder reactions have been developed and often a mechanism has been demonstrated to be a double addition rather than synchronous. This review aims to cover literature up to the end of 2010, describing all the different organocatalytic asymmetric 1,4-conjugate additions even if they are listed as transfer hydrogenation, cycloadditions or desymmetrization of aromatic compounds.
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