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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
Author(s) -
Lemonnier Gérald,
Poisson Thomas,
CouveBonnaire Samuel,
Jubault Philippe,
Pannecoucke Xavier
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300140
Subject(s) - diethylzinc , chemistry , amide , imine , organic chemistry , medicinal chemistry , catalysis , enantioselective synthesis
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.