Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations

We report a novel, efficient, and easily prepared substrate/precursor family of Schiff bases of various glycine esters with 2-hydroxybenzophenone, and their use for the synthesis of amino acids in quantitative yields. The Michael addition of the substrates to methyl acrylate gave two different types of product (cyclic or chain), depending on the nature of the base. Also, we demonstrated that one of the new substrates could be involved in an asymmetric version of the alkylation reaction (70% ee).

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ChemInform Abstract: ASYMMETRIC SYNTHESIS OF THREONINE AND PARTIAL RESOLUTION AND RETRORACEMIZATION OF α-AMINO ACIDS VIA COPPER(II) COMPLEXES OF THEIR SCHIFF BASES WITH (S)-2-N-(N′-BENZYLPROLYL)AMINOBENZALDEHYDE AND (S)-2-N-(N′-BENZYLPROLYL)AMINOACETOPHEN

Chemischer Informationsdienst ◽

10.1002/chin.198328315 ◽

1983 ◽

Vol 14 (28) ◽

Author(s):

YU. N. BELOKON ◽

I. E. ZEL'TZER ◽

V. I. BAKHMUTOV ◽

M. B. SAPOROVSKAYA ◽

M. G. RYZHOV ◽

...

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Schiff Bases ◽

Partial Resolution

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Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations

ChemInform Abstract: Asymmetric Synthesis of α-Amino Acids via Homologation of Ni(II) Complexes of Glycine Schiff Bases. Part 3. Michael Addition Reactions and Miscellaneous Transformations

ChemInform Abstract: Michael Addition Reactions Between Nucleophilic Glycine Equivalents and Acrylic Acid Derivatives as a Practical and Generalized Approach to the Asymmetric Synthesis of Î²-Substituted Î±-Amino Acids

ChemInform Abstract: Asymmetric Synthesis of α-Amino Acids via Homologation of Ni(II) Complexes of Glycine Schiff Bases. Part 2. Aldol, Mannich Addition Reactions, Deracemization and (S) to (R) Interconversion of α-Amino Acids

Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 2: Aldol, Mannich addition reactions, deracemization and (S) to (R) interconversion of α-amino acids

Amino Acids. XV. Michael Addition Reactions of Diethyl Acetamidomalonate1

Asymmetric Synthesis of β-Amino Acids via the Michael Addition of Chiral Metal Amides

ChemInform Abstract: Asymmetric Synthesis of α-Amino Acids via Homologation of Ni(II) Complexes of Glycine Schiff Bases. Part 1. Alkyl Halide Alkylations

Asymmetric Synthesis of 3-Methylthio Alcohols by Intramolecular Michael Addition Reactions.

Economical Synthesis of α-Amino Acids from a Novel Family of Easily Available Schiff Bases of Glycine Esters and 2-Hydroxy­benzophenone

ChemInform Abstract: ASYMMETRIC SYNTHESIS OF THREONINE AND PARTIAL RESOLUTION AND RETRORACEMIZATION OF α-AMINO ACIDS VIA COPPER(II) COMPLEXES OF THEIR SCHIFF BASES WITH (S)-2-N-(N′-BENZYLPROLYL)AMINOBENZALDEHYDE AND (S)-2-N-(N′-BENZYLPROLYL)AMINOACETOPHEN

Economical Synthesis of α-Amino Acids from a Novel Family of Easily Available Schiff Bases of Glycine Esters and 2-Hydroxybenzophenone