2,2-Difluoro-1,3-diketones as gem-Difluoroenolate Precusors for Asymmetric Aldol Addition with N-Benzylisatins
2,2-Difluoro-1,3-diketones are introduced as gem-difluoroenolate precursors for the first example of an organocatalytic asymmetric aldol addition with N-benzylisatins to form 3-difluoroalkyl-3-hydroxyoxindoles. (Figure presented.).
Qian, Jinlong,Yi, Wenbin,Huang, Xin,Jasinski, Jerry P.,Zhang, Wei
Br?nsted acid-catalyzed enantioselective addition of 1,3-diones to in situ generated N-acyl ketimines
A Br?nsted acid-catalyzed asymmetric Mannich-type addition of 1,3-diones to cyclic N-acyl ketimines is reported for the synthesis of enantioenriched isoindolinones. Various dicarbonyl-substituted isoindolinones bearing a quaternary carbon stereocenter were synthesized with excellent yields (up to 98%) and moderate to high enantioselectivities (up to 95% ee), and most of them possess a fluorine atom at the reactive center. Furthermore, the synthetic utility of the protocol has been demonstrated by the debenzoylation of the product.
Sadhu, Milon M.,Ray, Sumit K.,Unhale, Rajshekhar A.,Singh, Vinod K.
supporting information
p. 410 - 414
(2022/01/20)
Organocatalytic Asymmetric Cascade Michael-acyl Transfer Reaction between 2-Fluoro-1,3-diketones and Unsaturated Thiazolones: Access to Fluorinated 4-Acyloxy Thiazoles
Quinine derived bifunctional urea catalyzed cascade Michael-acyl transfer reaction of 5-alkenyl thiazolones and monofluorinated β-diketones has been developed. The fluorine containing 4-acyloxy thiazoles were synthesized in high yields and good diastereo-and excellent enantioselectivities. Synthetic transformations, including synthesis of 4-hydroxy thiazoles, have been demonstrated.
Biswas, Rayhan G.,Ray, Sumit K.,Unhale, Rajshekhar A.,Singh, Vinod K.
supporting information
p. 6504 - 6509
(2021/08/30)
Regioselective Rhodium-Catalyzed Addition of 1,3-Dicarbonyl Compounds to Terminal Alkynes
A new method for the rhodium-catalyzed regioselective C-C bond formation using terminal alkynes and 1,3-dicarbonyl compounds to achieve valuable branched α-allylated 1,3-dicarbonyl products is reported. With a Rh(I)/DPEphos/p-CF3-benzoic acid as the catalyst system, the desired products can be obtained in good to excellent yields and with perfect regioselectivity. A broad range of functional groups were tolerated, and first experimental insights of a plausible reaction mechanism were obtained.
Beck, Thorsten M.,Breit, Bernhard
supporting information
p. 124 - 127
(2016/01/15)
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