One-Pot Chemoenzymatic Cascade for the Enantioselective C(1)-Allylation of Tetrahydroisoquinolines

Sangster, Jack J.; Ruscoe, Rebecca E.; Cosgrove, Sebastian C.; Mangas-Sánchez, Juan; Turner, Nicholas J.

Abstract

Herein, we report a one-pot, chemoenzymatic process for the synthesis of enantioenriched C(1)-allylated tetrahydroisoquinolines. This transformation couples a monoamine oxidase (MAO-N)-catalyzed oxidation with a metal catalyzed allylboration, followed by a biocatalytic deracemization to afford allylic amine derivatives in both high yields and good to high enantiomeric excess. The cascade is operationally simple, with all components added at the start of the reaction and can be used to generate key building blocks for further elaboration.

• Journal Article Type: Article
• Acceptance Date: Feb 15, 2023
• Online Publication Date: Feb 15, 2023
• Publication Date: Mar 1, 2023
• Deposit Date: May 30, 2023
• Journal: Journal of the American Chemical Society
• Print ISSN: 0002-7863
• Electronic ISSN: 1520-5126
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 145
• Issue: 8
• Pages: 4431-4437
• DOI: https://doi.org/10.1021/jacs.2c09176
• Keywords: Colloid and Surface Chemistry; Biochemistry; General Chemistry; Catalysis