95932-32-4Relevant articles and documents
Formal α-Allylation of Primary Amines by a Dearomative, Palladium-Catalyzed Umpolung Allylation of N-(Aryloxy)imines
Mori-Quiroz, Luis M.,Londhe, Shrikant S.,Clift, Michael D.
, p. 14827 - 14846 (2020/12/02)
N-(Aryloxy)imines, readily accessible by condensation/tautomerization of (pseudo)benzylic primary amines and 2,6-di-tert-butyl-1,4-benzoquinone, undergo efficient allylation to afford a wide range of homoallylic primary amines following hydrolytic workup. Deprotonation of N-(aryloxy)imines generates a delocalized 2-azaallyl anion-type nucleophile that engages in dearomative C-C bond-forming reactions with allylpalladium(II) electrophiles generated from allylic tert-butyl carbonates. This reactivity umpolung enables the formal α-allylation of (pseudo)benzylic primary amines. Mechanistic studies reveal that the apparent regioselectivity of the desired bond-forming event is a convergent process that is initiated by unselective allylation of N-(aryloxy)imines to give several regioisomeric species, which subsequently rearrange via stepwise [1,3]- or concerted [3,3]-sigmatropic shifts, ultimately converging to provide the desired regioisomer of the amine products.
Ouabain 19-site primary hydroxyl derivative as well as preparation method and application thereof
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Paragraph 0063-0067; 0083-0085, (2020/12/05)
The invention provides an ouabain 19-site primary hydroxyl derivative as well as a preparation method and application thereof. The structure of the ouabain 19-site primary hydroxyl derivative is shownas a formula I. The derivative has very low toxicity to normal cells and also has an excellent effect of inhibiting tumor cells. In addition, the derivative can effectively inhibit tumor cell migration and invasion. Therefore, the ouabain 19-site primary hydroxyl derivative has a very good application prospect in preparation of drugs for resisting tumors and inhibiting tumor invasion and/or migration.
Stereodivergent allylic substitutions with aryl acetic acid esters by synergistic iridium and lewis base catalysis
Jiang, Xingyu,Beiger, Jason J.,Hartwig, John F.
, p. 87 - 90 (2017/05/16)
The preparation of all possible stereoisomers of a given chiral molecule bearing multiple stereocenters by a simple and unified method is a significant challenge in asymmetric catalysis. We report stereodivergent allylic substitutions with aryl acetic acid esters catalyzed synergistically by a metallacyclic iridium complex and benzotetramisole. Through permutations of the enantiomers of the two chiral catalysts, all four stereoisomers of the products bearing two adjacent stereocenters are accessible with high diastereoselectivity and enantioselectivity. The resulting chiral activated ester products can be converted readily to enantioenriched amides, unactivated esters, and carboxylic acids in a onepot manner.
