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

Institutions

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
Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Synthesis of α,α-difluoro-β-amino amides using aldimines and bromodifluoroacetamides via the Reformatsky reaction

Ryota Ozawa, Tetsuya Yamamoto
2 links
Organic & Biomolecular Chemistry
Fluorine in Organic Chemistry
article

Synthesis of α,α-difluoro-β-amino amides using aldimines and bromodifluoroacetamides via the Reformatsky reaction

Ryota Ozawa, Tetsuya Yamamoto
article en

Abstract

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>.

Organic & Biomolecular ChemistryVol. 23(18)
Tokyo Denki University (JP)
Openalex Percentile: Top 95%
Fluorine in Organic Chemistry
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.