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Literature DB >> 23679128

Biomimetic asymmetric 1,3-dioplar cycloaddition: amino acid precursors in biosynthesis serve as latent azomethine ylides.

Abstract

The first asymmetric catalytic biomimetic three-component 1,3-dipolar cycloaddition of α-keto esters and benzylamine with electron-deficient olefins, inspired by the transamination of α-keto acids involving pyridoxal phosphate (PLP)-dependent enzymes in biological systems, giving several families of structurally diverse pyrrolidine derivatives in high yields and excellent enantioselectivities (up to 99% ee) under mild conditions is described.

Entities: Chemical Gene

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Year: 2013 PMID： 23679128 DOI： 10.1021/ol400983j

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

7 in total

1. The Redox-A³ Reaction.

Authors: Daniel Seidel
Journal: Org Chem Front Date: 2014-06-01 Impact factor: 5.281

2. Catalytic Asymmetric Synthesis of Chiral γ-Amino Ketones via Umpolung Reactions of Imines.

Authors: Lin Hu; Yongwei Wu; Zhe Li; Li Deng
Journal: J Am Chem Soc Date: 2016-11-30 Impact factor: 15.419

3. Catalytic, enantioselective 1,3-dipolar cycloadditions of nitrile imines with methyleneindolinones.

Authors: Anthony L Gerten; Michael C Slade; Kelsie M Pugh; Levi M Stanley
Journal: Org Biomol Chem Date: 2013-10-17 Impact factor: 3.876

4. Synthesis of α-CF₃-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors.

Authors: Michael Winter; Kirill Faust; Markus Himmelsbach; Mario Waser
Journal: Org Biomol Chem Date: 2019-06-12 Impact factor: 3.876

Biomimetic asymmetric 1,3-dioplar cycloaddition: amino acid precursors in biosynthesis serve as latent azomethine ylides.

1. The Redox-A³ Reaction.

2. Catalytic Asymmetric Synthesis of Chiral γ-Amino Ketones via Umpolung Reactions of Imines.

3. Catalytic, enantioselective 1,3-dipolar cycloadditions of nitrile imines with methyleneindolinones.

4. Synthesis of α-CF₃-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors.

Review 5. Kitamura Electrophilic Fluorination Using HF as a Source of Fluorine.

6. A new entry to azomethine ylides from allylic amines and glyoxals: shifting the reliance on amino ester precursors.

7. Pd-Catalyzed Allylation of Imines to Access α-CF₃-Substituted α-Amino Acid Derivatives.

Biomimetic asymmetric 1,3-dioplar cycloaddition: amino acid precursors in biosynthesis serve as latent azomethine ylides.

1. The Redox-A3 Reaction.

2. Catalytic Asymmetric Synthesis of Chiral γ-Amino Ketones via Umpolung Reactions of Imines.

3. Catalytic, enantioselective 1,3-dipolar cycloadditions of nitrile imines with methyleneindolinones.

4. Synthesis of α-CF3-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors.

Review 5. Kitamura Electrophilic Fluorination Using HF as a Source of Fluorine.

6. A new entry to azomethine ylides from allylic amines and glyoxals: shifting the reliance on amino ester precursors.

7. Pd-Catalyzed Allylation of Imines to Access α-CF3-Substituted α-Amino Acid Derivatives.

1. The Redox-A³ Reaction.

4. Synthesis of α-CF₃-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors.

7. Pd-Catalyzed Allylation of Imines to Access α-CF₃-Substituted α-Amino Acid Derivatives.