基于保护基的铱催化左旋多巴的C-H硼化反应

Yang Cliff, Fan Jinda, Maleczka Robert E

Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824, United States.

Department of Radiology, Michigan State University, 846 Service Road, East Lansing, Michigan 48824, United States.

J Org Chem. 2025 Jun 6;90(22):7507-7509. doi: 10.1021/acs.joc.5c00476. Epub 2025 May 27.

Despite being an important aromatic amino acid, iridium-catalyzed borylation (CHB) of levodopa has not been reported. Via the application of carefully chosen protecting groups for the catechol moiety, the steric hindrance around the arene can be reduced, enabling selective C5 CHB of levodopa. Methylene and boronic ester protecting groups were explored, the latter of which is deprotected in situ to yield the free catechol.

尽管左旋多巴是一种重要的芳香族氨基酸，但铱催化的左旋多巴硼氢化反应（CHB）尚未见报道。通过为儿茶酚部分精心选择保护基团，可以减少芳烃周围的空间位阻，从而实现左旋多巴的选择性C5硼氢化反应。研究了亚甲基和硼酸酯保护基团，其中后者可原位脱保护生成游离儿茶酚。