1374328-83-2Relevant academic research and scientific papers
1-(Trifluoromethyl)cyclopent-3-enecarboxylic acid derivatives: Platforms for bifunctional cyclic trifluoromethyl building blocks
Grellepois, Fabienne,Kikelj, Vincent,Coia, Nicolas,Portella, Charles
, p. 509 - 517 (2012)
We report herein the synthesis and applications of 1-(trifluoromethyl) cyclopent-3-ene-1-carboxylic acid and itsesters, promising new trifluoromethylated cyclic building blocks. Initially prepared starting from a pentafluorodithiopropanoic ester, a more convenient and effective approach has been developed starting from commercially available trifluoropropanoic acid or its methyl ester. The interest in these building blocks is exemplified by their use as platforms for a variety of difunctional trifluoromethylcyclopentane derivatives. We disclose herein a promising new building block, 1-(trifluoromethyl)cyclopent-3-enecarboxylic acid (and its esters), accessible in high yield from commercially available trifluoropropanoic acid derivatives. These building blocks exhibit high synthetic potential, given the reaction diversity offered by the double bond and thecarboxylic function. Copyright
Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling
Hoang, Gia L.,Yang, Zhao-Di,Smith, Sean M.,Miska, Judy L.,Prez, Damaris E.,Zeng, Xiao Cheng,Takacs, James M.,Pal, Rhitankar,Pelter, Libbie S. W.
supporting information, p. 940 - 943 (2015/03/30)
The rhodium-catalyzed enantioselective desymmetrization of symmetric γ,δ-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral γ-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.
