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Synfacts 2005(0): 0065-0065  
DOI: 10.1055/s-2005-869927
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Modular Catalysts for the Enantioselective Allylation of Aldehydes

Contributor(s): Paul Knochel, Andrei Gavryushin
J.-Y. Lee, J. J. Miller, S. S. Hamilton, M. S. Sigman*
University of Utah, USA
Stereochemical Diversity in Chiral Ligand Design: Discovery and Optimization of Catalysts for the Enantioselective Addition of Allylic Halides to Aldehydes
Org. Lett.  2005,  7:  1837-1839  
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Publication History

Publication Date:
20 July 2005 (online)

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Key words

asymmetric synthesis - allylation - modular ligands

Significance

The formerly developed Mn-Cr(II)-mediated allylation of aldehydes for the first time has been performed in an enantioselective variant using a set of modular amino acid-derived ligands. Enantioselectivities of up to 95% were achieved after screening of different catalyst diastereomers.

Comment

A modular approach for the search for new enantioselective ligands is very promising as it offers a rational method for improving the enan­tioselectivity by changing the building blocks at will. Modular ligands can be developed for most metal-catalyzed reactions, starting usually from available naturally occurring materials, in several simple steps.

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