Nonproteingenic a-, or �-amino acids have attracted tremendous attention, they are widely utilized for biological, biochemical, pharmaceutical, and asymmetric chemical investigations. The nickel(II) complex has been widely used to synthesize enantiopure amino acids via aldol, Michael addition, Mannich reaction, and C-alkylation reactions. Notable merits of the nickel(II) complex's methods include: (1) predictable stereochemical outcome and high level of enantio- and/or diastereoselectivity; (2) inexpensive cost-structure and ready availability of nickel(II) complexes; (3) operationally convenient reaction procedures; (4) high overall reaction yields and reproducibility; and (5) easy and virtually complete recovery of chiral ligands, rivaling catalytic methods in terms of consumption of the stereocontrolling reagents. These unique features render this method an attractive strategy for practical synthesis of various a- and �-amino acids, in particular on relatively large scale. Recently, we developed a new strategy for preparing the chiral Ni(II) complex for the asymmetric synthesis of chiral amino acids. We applied this new method in our new progress of chiral Ni(II) complex for the asymmetric Mannich reaction to synthesis enantiopure a,�-diamino acids, the enantioselective tandem conjugate addition-elimination reaction to synthesis glutamic acid derivatives, the Suzuki coupling reaction to synthesis �2-amino acid derivatives, the asymmetric Mannich reaction to synthesis of 3-aminoaspartate, the asymmetric Michael addition reaction to synthesis �-substituted-a,?-diaminobutyric acid derivatives, the asymmetric alkylation reaction to synthesis linear ?-trifluoromethyl containing amino acids, the asymmetric Michael addition reaction to synthesis of syn-�-substituted tryptophans, the asymmetric Diels-Alder reaction to synthesis cyclic amino acid derivatives, the asymmetric oxidative heterocoupling reaction for 3-indolylglycines, and the asymmetric oxidative cross-dehydrogenative coupling reaction for tetrahydroisoquinolin-1-yl glycine derivatives.

Apply Ni(II) complexes to efficient asymmetric synthesis of chiral a- and �-amino acids

248th National Meeting (2014)

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