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Cu(I)/Chiral Phosphoric Acid-Catalyzed Radical-Involved Enantioselective Intramolecular Amination of Allylic and Benzylic C-H Bonds.

07:00 EST 8th November 2019 | BioPortfolio

Summary of "Cu(I)/Chiral Phosphoric Acid-Catalyzed Radical-Involved Enantioselective Intramolecular Amination of Allylic and Benzylic C-H Bonds."

Radical-involved enantioselective oxidative C-H bond functionalization via a hydrogen atom transfer (HAT) process has emerged as a promising method for accessing functionally diverse enantioenriched products, while asymmetric C(sp3)-H bond amination remains a formidable challenge. To address this problem, we herein describe a dual Cu(I)/chiral phosphoric acid (CPA) catalytic system for radical-involved enantioselective intramolecular C(sp3)-H amination of not only allylic positions but also benzylic positions with broad substrate scope. The use of 4-OMe-NHPI as a stable and chemoselective HAT mediator precursor is crucial for the fulfillment of this transformation. Preliminary mechanistic studies indicate that a crucial allylic or benzylic radical intermediate resulting from a HAT process is involved.

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This article was published in the following journal.

Name: Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
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Medical and Biotech [MESH] Definitions

Inorganic derivatives of phosphoric acid (H3PO4). Inorganic salts are known as PHOSPHATES and organic esters are PHOSPHORIC ACID ESTERS.

Amide derivatives of phosphoric acid such as compounds that include the phosphoric triamide (P(=O)(N)(N)(N)) structure.

Derivatives of phosphatidic acids in which the phosphoric acid is bound in ester linkage to a serine moiety. Complete hydrolysis yields 1 mole of glycerol, phosphoric acid and serine and 2 moles of fatty acids.

Derivatives of phosphatidic acids in which the phosphoric acid is bound in ester linkage to an ethanolamine moiety. Complete hydrolysis yields 1 mole of glycerol, phosphoric acid and ethanolamine and 2 moles of fatty acids.

Derivatives of phosphatidic acids in which the phosphoric acid is bound in ester linkage to a choline moiety. Complete hydrolysis yields 1 mole of glycerol, phosphoric acid and choline and 2 moles of fatty acids.

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