Aminocatalytic remote functionalization strategies

Chemical Science Pub Date: 2013-03-15 DOI: 10.1039/C3SC50405K

Abstract

The recent development in organocatalytic remote functionalization strategies will be outlined. The application of aminocatalysis for the activation of unsaturated carbonyl compounds has led to tremendous development of new interesting methodologies providing chiral frameworks relevant for life-science. Spectacular examples of chirality relayed to a new stereogenic centers located at five (for γ-functionalizations) to seven (for ε-functionalizations) bonds away from the stereodifferentiating element of the aminocatalyst will be demonstrated. The site-specificity of these strategies is particularly intriguing and it will be outlined how such regioselectivity is controlled by the substitution patterns of the starting carbonyl compounds. Furthermore, in most of the cases these aminocatalytic remote functionalizations proceed with high enantio- and diastereoselectivities. The applied aminocatalysts govern the stereochemical outcome of the reactions by either the steric shielding or the hydrogen-bond directing principle. One very important aspect of these two stereodifferentiating approaches is their complementarity, opening access to a variety of enantioenriched acyclic, hetero- and carbocyclic compounds. The application of remote functionalization approaches as the key steps in the total synthesis of several natural products or drugs will also be presented.

Graphical abstract: Aminocatalytic remote functionalization strategies
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