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Highly Efficient Synthesis of Heterocyclic and Alicyclic β 2 ‐Amino Acid Derivatives by Catalytic Asymmetric Hydrogenation
Author(s) -
Li Lanning,
Chen Bin,
Ke Yuanyuan,
Li Qing,
Zhuang Yue,
Duan Kun,
Huang Yichun,
Pang Jiyan,
Qiu Liqin
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201300339
Subject(s) - alicyclic compound , enantioselective synthesis , catalysis , chemistry , substrate (aquarium) , organic chemistry , asymmetric hydrogenation , combinatorial chemistry , rhodium , reactivity (psychology) , oceanography , alternative medicine , pathology , geology , medicine
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.