A new enantioselective synthesis of β-amino acids

Enantioselective hydrogenation of some α,β-unsaturated nitriles and their corresponding methyl esters bearing a phthalimidomethyl substituent at the α-carbon using Rh-DuPHOS catalysts afforded β-amino acid precursors with modest e.e.s of up to 48%. Hydrogenation of the α,β-unsaturated methyl esters...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2001-03, Vol.12 (4), p.657-667
Main Authors: Saylik, Dilek, Campi, Eva M., Donohue, Andrew C., Jackson, W.Roy, Robinson, Andrea J.
Format: Article
Language:English
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Summary:Enantioselective hydrogenation of some α,β-unsaturated nitriles and their corresponding methyl esters bearing a phthalimidomethyl substituent at the α-carbon using Rh-DuPHOS catalysts afforded β-amino acid precursors with modest e.e.s of up to 48%. Hydrogenation of the α,β-unsaturated methyl esters using a Ru-BINAP catalyst gave higher e.e.s of up to 84%. Method development for the determination of the enantiomeric excesses of these derivatives using chiral HPLC is also reported. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(01)00097-0