The enantioselective organocatalytic methodologies described in this chapter are a clear demonstration of the enormous potentiality of metal-free catalytic reductions. Despite the historical need for and continued interest in chiral amines, their synthesis remains challenging. In one case, binaphthol-derived phosphoric acids have been successfully employed in a process that involves the use of a dihydropyridine-based compound as the reducing agent. In another strategy the reducing agent is trichlorosilane; finally in the very last few years a novel approach has been developed to realize metal-free hydrogenation of imines: The Frustrated Lewis Pair (FLP) method involves the use of a combination of a strong Lewis acid with a variety of sterically encumbered Lewis bases to activate hydrogen at ambient conditions. It is recognized that these chemical adducts could find application in catalytic hydrogenation reactions.

Enantioselective organocatalytic reductions / M. Benaglia, M. Bonsignore, A. Genoni - In: Stereoselective organocatalysis : bond formation methodologies and activation modes / [a cura di] R. Rios Torres. - Hoboken : Wiley, 2013. - ISBN 9781118203538. - pp. 529-558 [10.1002/9781118604755.ch15]

Enantioselective organocatalytic reductions

M. Benaglia;M. Bonsignore;A. Genoni
2013

Abstract

The enantioselective organocatalytic methodologies described in this chapter are a clear demonstration of the enormous potentiality of metal-free catalytic reductions. Despite the historical need for and continued interest in chiral amines, their synthesis remains challenging. In one case, binaphthol-derived phosphoric acids have been successfully employed in a process that involves the use of a dihydropyridine-based compound as the reducing agent. In another strategy the reducing agent is trichlorosilane; finally in the very last few years a novel approach has been developed to realize metal-free hydrogenation of imines: The Frustrated Lewis Pair (FLP) method involves the use of a combination of a strong Lewis acid with a variety of sterically encumbered Lewis bases to activate hydrogen at ambient conditions. It is recognized that these chemical adducts could find application in catalytic hydrogenation reactions.
catalytic hydrogenation ; chiral phosphoric acids ; enantioselective organocatalytic reduction ; frustrated Lewis pair (FLP) ; richlorosilane
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/244247
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