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Chapter 3

Enantioselective Conjugate Addition Reactions via Iminium Activation

Primary and secondary amines can catalyze the conjugate addition reaction of different carbon and heteroatom-centered nucleophiles to α,β-unsaturated aldehydes or ketones via reversible formation of an iminium intermediate. This reactivity profile together with the possibility of introducing chiral information in different places of the catalyst structure has led to the development of many different methodologies for carrying out enantioselective Michael reactions applying this concept. The availability of many different Michael donors (nitroalkanes, 1,3-dicarbonyl compounds, Hantzsch esters, electron-rich aromatic compounds, amines, oximes, phosphines or thiols among others) turns this methodology an extremely powerful tool for the preparation of many different chiral building blocks. In this chapter, the different methodologies developed for carrying out conjugate addition reactions in an stereocontrolled way using this iminium activation concept will be disclosed which have been organized according to the nature of the Michael donor employed.

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18 Oct 2010
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From the book series:
Catalysis Series