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Symmetry 2011, 3(1), 84-125; doi:10.3390/sym3010084

Asymmetric Organocatalytic Reactions of α,β-Unsaturated Cyclic Ketones

1
Department of Chemistry, University of Calabria, Ponte Bucci cubo 12/c, I-87030 Arcavacata di Rende (Cs), Italy
2
Department of Organic Chemistry “A. Mangini”, University of Bologna, viale Risorgimento 4, I-40136 Bologna, Italy
*
Author to whom correspondence should be addressed.
Received: 18 February 2011 / Revised: 8 March 2011 / Accepted: 9 March 2011 / Published: 22 March 2011
(This article belongs to the Special Issue Asymmetric Organocatalysis)
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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.
Keywords: α,β-unsaturated ketones; organocatalysis; iminium ion; Michael addition α,β-unsaturated ketones; organocatalysis; iminium ion; Michael addition
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Dalpozzo, R.; Bartoli, G.; Bencivenni, G. Asymmetric Organocatalytic Reactions of α,β-Unsaturated Cyclic Ketones. Symmetry 2011, 3, 84-125.

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