Highly efficient synthesis of heterocyclic and alicyclic β2-amino acid derivatives by catalytic asymmetric hydrogenation.

TitleHighly efficient synthesis of heterocyclic and alicyclic β2-amino acid derivatives by catalytic asymmetric hydrogenation.
Publication TypeJournal Article
Year of Publication2013
AuthorsLi L, Chen B, Ke Y, Li Q, Zhuang Y, Duan K, Huang Y, Pang J, Qiu L
JournalChemistry, an Asian journal
Volume8
Issue9
Pagination2167-74
Date Published2013 Sep
Abstract

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.

DOI10.3978/j.issn.2223-4292.2013.06.06
Alternate JournalChem Asian J