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Highly efficient synthesis of heterocyclic and alicyclic β2-amino acid derivatives by catalytic asymmetric hydrogenation.
|Title||Highly efficient synthesis of heterocyclic and alicyclic β2-amino acid derivatives by catalytic asymmetric hydrogenation.|
|Publication Type||Journal Article|
|Year of Publication||2013|
|Authors||Li L, Chen B, Ke Y, Li Q, Zhuang Y, Duan K, Huang Y, Pang J, Qiu L|
|Journal||Chemistry, an Asian journal|
|Date Published||2013 Sep|
A valuable class of new heterocyclic and alicyclic prochiral α-aminomethylacrylates has been conveniently synthesized through a three-step transformation involving a Baylis-Hillman reaction, O-acetylation, and a subsequent allylic amination. The corresponding novel β(2)-amino acid derivatives were prepared with excellent enantioselectivities and high yields by catalytic asymmetric hydrogenation using the catalyst rhodium(Et-Duphos) (Et-Duphos = 2',5',2'',5''-tetraethyl-1,2-bis(phospholanyl)benzene)) under mild reaction conditions (up to 99 % ee and S/C = 1000). The influence of the substrate on the enantioselectivity and reactivity is investigated, and the most suitable substrate configuration for the highly efficient enantioselective hydrogenation of β-substituted α-aminomethylacrylates under the Rh-Duphos system is reported. The current protocol provides a very practical, facile, and scalable method for the preparation of heterocyclic and alicyclic β(2)-amino acids and their derivatives.
|Alternate Journal||Chem Asian J|