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Non-metallocene Rare Earth Metal Catalysts for the Diastereoselective and Enantioselective Hydroamination of Aminoalkenes by Kai C. Hultzsch; Denis V. Gribkov; Frank Hampel is a Chemistry article available to read on EtoBox.

What is Non-metallocene Rare Earth Metal Catalysts for the Diastereoselective and Enantioselective Hydroamination of Aminoalkenes about?

In this short review we summarize our work on new cyclopentadienyl-free rare earth metal catalysts for the diastereoselective and enantioselective hydroamination of aminoalkenes. Non-metallocene rare earth metal catalysts based on diamidoamine, biphenolate and binaphtholate ligands are readily available through alkane and amine elimination procedures. Diamidoamine yttrium complexes are efficient catalysts for the highly diastereoselective cyclization of 1-methyl-pent-4-enylamine to yield trans-2,5-dimethyl-pyrroldine with trans to cis ratios of up to 23:1. The X-ray crystal structural analysis of [((2,6-Et 2 C 6 -H 3 NCH 2 CH 2 ) 2 NMe)Y{N(SiMe 3 ) 2 }] is reported in which yttrium is coordinated in a highly distorted tetrahedral fashion. 3,3 0 -Di-tert-butyl substituted biphenolate complexes tend to form phenolate-bridged hetero-and homochiral dimers. The low steric demand of the tert-butyl substituents resulted also in low enantioselectivities in hydroamination/cyclization reactions. Binaphtholate complexes with sterically more demanding tris(aryl)silyl substituents were more efficient catalysts; giving enantioselectivities of up to 83% ee. These catalysts could also be applied i

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Author

Kai C. Hultzsch; Denis V. Gribkov; Frank Hampel

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-328X)

Published

2005

Language

EN

Field

Chemistry (Physical Sciences)