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Chapter 4

Enantioselective Conjugate Addition Reactions via Hydrogen-bonding Activation

The interaction of a Brønsted acid with the Michael acceptor via the formation of a hydrogen bond releases electron density from the olefin, resulting in the activation of the later towards conjugate addition reaction in the presence of a suitable nucleophile. In this chapter, the methods developed to carry out Michael-type reactions using catalysts operating through this kind of mechanism will be presented, showing that this possibility is a good alternative to metal-catalyzed reactions and also to the already shown enamine- and iminium-mediated transformations. By the clever application of the H-bonding activation concept, a wide variety of methodologies for the addition of carbon- and heteroatom-centered nucleophiles to electron-deficient olefins, together with several examples of conjugate reductions will be presented. As it has been done in the previous chapter, these will be organized according to the nature of the nucleophile and the Michael acceptor employed.

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18 Oct 2010
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From the book series:
Catalysis Series