Diethylzinc-Mediated Addition of 2,2-Dibromo-2-fluoroacetamides to Carbonyl Compounds: Synthesis of α-Bromo-α-fluoro-β-hydroxy Amides and/or (Z)-Fluorovinyl Amides

We describe straightforward routes either to α‐bromo‐α‐fluoro‐β‐hydroxy amides or to (Z)‐α‐fluoroacrylamides starting from aldehydes, ketones or imine and 2,2‐dibromo‐2‐fluoroacetamides. Depending on the nature of the amide, these diethylzinc‐mediated additions to aldehydes, ketones or imine afford...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2013-06, Vol.2013 (16), p.3278-3289
Main Authors: Lemonnier, Gérald, Poisson, Thomas, Couve-Bonnaire, Samuel, Jubault, Philippe, Pannecoucke, Xavier
Format: Article
Language:English
Subjects:
Aldehydes
Chemical Sciences
Fluorine
Olefination
Organic chemistry
Synthetic methods
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We describe straightforward routes either to α‐bromo‐α‐fluoro‐β‐hydroxy amides or to (Z)‐α‐fluoroacrylamides starting from aldehydes, ketones or imine and 2,2‐dibromo‐2‐fluoroacetamides. Depending on the nature of the amide, these diethylzinc‐mediated additions to aldehydes, ketones or imine afford selective access either to bromofluorohydrins or to (Z)‐α‐fluoroacrylamides. The corresponding products were obtained in moderate to very good yields and the configurations of both products were confirmed by X‐ray analyses. Reactions between aldehydes, ketones or imines and 2,2‐dibromo‐2‐fluoroacetamides, a new class of fluorinated reagent, allow straightforward selective access to α‐bromo‐α‐fluoro‐β‐hydroxy amides and/or (Z)‐α‐fluoroacrylamides with moderate to excellent yields.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300140