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Construction of Trifluoromethyl‐Bearing Quaternary Carbon Centers by Intramolecular Decarboxylative Allylation of α‐Trifluoromethyl β‐Keto Esters
Author(s) -
Shibata Norio,
Suzuki Satoru,
Furukawa Tatsuya,
Kawai Hiroyuki,
Tokunaga Etsuko,
Yuan Zhe,
Cahard Dominique
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100359
Subject(s) - chemistry , trifluoromethyl , tetrahydrofuran , medicinal chemistry , intramolecular force , palladium , fluoride , quaternary carbon , tris , catalysis , organic chemistry , alkyl , enantioselective synthesis , inorganic chemistry , biochemistry , solvent
A new palladium‐catalyzed decarboxylative allylation of allyl α‐trifluoromethyl‐β‐keto esters was developed in the presence of tris(dibenzylideneacetone)dipalladium [Pd 2 (dba) 3 ] and 1,2‐bis(diphenylphosphino)ethane (dppe) in tetrahydrofuran. α‐Trifluoromethyl ketones featuring a quaternary carbon center were produced in good yields and the dreaded α,β‐unsaturated‐β,β‐difluoro ketones resulting from β‐elimination of a fluoride ion was not observed.