M. Burk, J. Allen, W. Kiesman
Jan 16, 1998
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Journal
Journal of the American Chemical Society
Abstract
An extremely efficient method has been found for the catalytic asymmetric hydrogenation of conjugated α,γ-dienamide esters using the Et-DuPHOS-Rh catalyst system. α,γ-Dienamide ester substrates were prepared via the Suzuki cross-coupling reaction and the Horner−Emmons olefination. Full conversion to the corresponding γ,δ-unsaturated amino acids with very high regio- and enantioselectivity was achieved after short reaction times. This new methodology was applied to the synthesis of the natural product bulgecinine from a prochiral dienamide ester.