Synthesis of α,α-difluoro-β-amino amides using aldimines and bromodifluoroacetamides <i>via</i> the Reformatsky reaction
α,α-Difluoro-β-amino amides are attractive building blocks of biologically active compounds such as fluorinated pharmaceutical mimics and oligopeptides. Herein, we describe the zinc-promoted Reformatsky reaction of aldimines using bromodifluoroacetamides which provides a direct synthetic approach to α,α-difluoro-β-amino amides. This method gave various <i>N</i>-PMP protected α,α-difluoro-β-amino-β-aryl amides in 64-95% yields. Furthermore, these amides were efficiently converted into 2,2-difluoropropane-1,3-diamines under reductive conditions using a combination of NaBH<sub>4</sub> and BF<sub>3</sub>.
Authors
- Ryota Ozawa
- Tetsuya Yamamoto (ORCID: https://orcid.org/0000-0002-1951-8956)
Institutions
- Tokyo Denki University (JP)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00388a
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00