- Spatiotemporal Control of Pre-existing Alkene Geometry: A Bio-Inspired Route to 4-Trifluoromethyl-2H-chromenes
-
Routes to prepare C4-trifluoromethyl analogues of the 2H-chromene scaffold are scarce: this is particularly striking given the importance of fluorine in pharmaceutical development. To address this limitation, a facile strategy has been developed that is reliant on catalytic, geometric isomerization of easily accessible allylic alcohols (up to >95:5) followed by intramolecular cyclization via Pd catalysis (up to 96%). This concise biomimetic approach emulates the photoisomerization/cyclization cascade inherent to phenylpropanoid biosynthesis.
- Fa?bender, Svenja I.,Metternich, Jan B.,Gilmour, Ryan
-
supporting information
p. 724 - 727
(2018/02/09)
-
- Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes
-
The traceless Petasis borono-Mannich reaction of enals, sulfonylhydrazines, and allylboronates, catalyzed by chiral biphenols, results in an asymmetric reductive transposition of the in situ generated allylic diazene. Acyclic 1,4-diene products bearing either alkyl- or aryl-substituted benzylic stereocenters are afforded in excellent yields and enantiomeric ratios of up to 99:1. The use of crotylboronates in the reaction results in concomitant formation of two stereocenters in either a 1,4-syn or anti relationship from the corresponding E- or Z-crotylboronate used in the reaction. The use of β-monosubstituted enals in the asymmetric traceless Petasis borono-Mannich reaction of crotylboronates installs tertiary methyl-bearing stereocenters in good yields and high enantioselectivities.
- Jiang, Yao,Thomson, Regan J.,Schaus, Scott E.
-
supporting information
p. 16631 - 16635
(2017/12/13)
-
- Synthesis of β-CF3 ketones from trifluoromethylated allylic alcohols by ruthenium catalyzed isomerization
-
This work describes the optimization process for the synthesis of β-trifluoromethylated ketones from trifluoromethylated allylic alcohols. This transformation proceeds through a ruthenium catalyzed isomerization under mild conditions with high atom econom
- Bizet, Vincent,Pannecoucke, Xavier,Renaud, Jean-Luc,Cahard, Dominique
-
-
- Construction of optically active CF3-containing quaternary carbon centers via stereospecific SN2′ reaction
-
(Chemical Equation Presented) Phosphates from 3-substituted 4,4,4-trifluorobut-2-en-1-ols were found to be effective for construction of CF3-containing quaternary carbon centers by way of Cu(I)-catalyzed Grignard reactions in the presence of ca
- Kimura, Mitsuo,Yamazaki, Takashi,Kitazume, Tomoya,Kubota, Toshio
-
p. 4651 - 4654
(2007/10/03)
-
- Synthese d'Amines Primaires Allyliques γ-trifluoromethylees
-
Des amines primaires allyliques substituees par un groupement trifluoromethyle ont ete preparees par une voie de synthese faisant intervenir intermediairement des azotures allyliques.Deux autres approches d'obtention de ces amines ont ete essayees: reacti
- Felix, Caroline,Laurent, Andre,Lebideau, Franck,Mison, Pierre
-
p. 2627 - 2648
(2007/10/02)
-