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Literature DB >> 33464093

α-C-H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines.

Jae Hyun Kim¹, Anirudra Paul¹, Ion Ghiviriga², Daniel Seidel¹.

Abstract

Enolizable cyclic imines, obtained in situ from their corresponding lithium amides by oxidation with simple ketone oxidants, are readily alkylated with a range of enolates to provide mono- and polycyclic β-aminoketones in a single operation, including the natural product (±)-myrtine. Nitrile anions also serve as competent nucleophiles in these transformations, which are promoted by BF3 etherate. β-Aminoesters derived from ester enolates can be converted to the corresponding β-lactams.

Entities: Chemical

Year: 2021 PMID： 33464093 PMCID： PMC7924990 DOI： 10.1021/acs.orglett.0c04024

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

55 in total

1. Photoredox-Catalyzed Site-Selective α-C(sp³ )-H Alkylation of Primary Amine Derivatives.

Authors: Melissa A Ashley; Chiaki Yamauchi; John C K Chu; Shinya Otsuka; Hideki Yorimitsu; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2019-02-15 Impact factor: 15.336

2. Tantalum catalyzed hydroaminoalkylation for the synthesis of α- and β-substituted N-heterocycles.

Authors: Philippa R Payne; Pierre Garcia; Patrick Eisenberger; Jacky C-H Yim; Laurel L Schafer
Journal: Org Lett Date: 2013-04-19 Impact factor: 6.005

3. Pseudophedrine-Derived Myers Enolates: Structures and Influence of Lithium Chloride on Reactivity and Mechanism.

Authors: Yuhui Zhou; Janis Jermaks; Ivan Keresztes; Samantha N MacMillan; David B Collum
Journal: J Am Chem Soc Date: 2019-03-21 Impact factor: 15.419

4. Assembling a Hybrid Pd Catalyst from a Chiral Anionic Co^III Complex and Ligand for Asymmetric C(sp³ )-H Functionalization.

Authors: Hua-Jie Jiang; Xiu-Mei Zhong; Jie Yu; Ying Zhang; Xinhao Zhang; Yun-Dong Wu; Liu-Zhu Gong
Journal: Angew Chem Int Ed Engl Date: 2018-12-21 Impact factor: 15.336

Review 5. Methylphenidate and its isomers: their role in the treatment of attention-deficit hyperactivity disorder using a transdermal delivery system.

Authors: David J Heal; David M Pierce
Journal: CNS Drugs Date: 2006 Impact factor: 5.749

6. Copper-Catalyzed Asymmetric Propargylation of Cyclic Aldimines.

Authors: Daniel R Fandrick; Christine A Hart; Ifeanyi S Okafor; Michael A Mercadante; Sanjit Sanyal; James T Masters; Max Sarvestani; Keith R Fandrick; Jennifer L Stockdill; Nelu Grinberg; Nina Gonnella; Heewon Lee; Chris H Senanayake
Journal: Org Lett Date: 2016-11-22 Impact factor: 6.005

7. Biomimetic Organocatalytic Approach to 4-Arylquinolizidine Alkaloids and Application in the Synthesis of (-)-Lasubine II and (+)-Subcosine II.

Authors: Seerat Virk; Sunil V Pansare
Journal: Org Lett Date: 2019-06-27 Impact factor: 6.005

8. Copper(I)-catalyzed enantioselective incorporation of ketones to cyclic hemiaminals for the synthesis of versatile alkaloid precursors.

Authors: Shi-Liang Shi; Xiao-Feng Wei; Yohei Shimizu; Motomu Kanai
Journal: J Am Chem Soc Date: 2012-10-08 Impact factor: 15.419

α-C-H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines.

1. Photoredox-Catalyzed Site-Selective α-C(sp³ )-H Alkylation of Primary Amine Derivatives.

2. Tantalum catalyzed hydroaminoalkylation for the synthesis of α- and β-substituted N-heterocycles.

3. Pseudophedrine-Derived Myers Enolates: Structures and Influence of Lithium Chloride on Reactivity and Mechanism.

4. Assembling a Hybrid Pd Catalyst from a Chiral Anionic Co^III Complex and Ligand for Asymmetric C(sp³ )-H Functionalization.

Review 5. Methylphenidate and its isomers: their role in the treatment of attention-deficit hyperactivity disorder using a transdermal delivery system.

6. Copper-Catalyzed Asymmetric Propargylation of Cyclic Aldimines.

7. Biomimetic Organocatalytic Approach to 4-Arylquinolizidine Alkaloids and Application in the Synthesis of (-)-Lasubine II and (+)-Subcosine II.

8. Copper(I)-catalyzed enantioselective incorporation of ketones to cyclic hemiaminals for the synthesis of versatile alkaloid precursors.

9. Direct Arylation of α-Amino C(sp³ )-H Bonds by Convergent Paired Electrolysis.

10. Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis.

1. Regioselective α-Cyanation of Unprotected Alicyclic Amines.

2. α-C-H/N-H Annulation of Alicyclic Amines via Transient Imines: Preparation of Polycyclic Lactams.

3. Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines.

Review 4. Recent progress in the chemistry of β-aminoketones.

5. α,α'-C-H Bond Difunctionalization of Unprotected Alicyclic Amines.