- Reactions of dimethoxycarbene with N-tosylated imines
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The reactions of dimethoxycarbene (DMC; 2), which was generated in situ by thermal decomposition of 2,5-dihydro-2,2-dimethoxy-5,5-dimethyl-l,3,4-oxadiazole (1), with N-tosylated imines of xanthone and 2,3:6,7-dibenzosuberenone, 3a and 3d, respectively, le
- Mloston, Grzegorz,Warkentin, John,Linden, Anthony,Heimgartner, Heinz
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- Organocatalytic nitrenoid transfer: Metal-free selective intermolecular C(sp3)-H amination catalyzed by an iminium salt
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This report details the first organocatalytic method for nitrenoid transfer and its application to intermolecular, site-selective C(sp3)-H amination. The method utilizes a trifluoromethyl iminium salt as the catalyst, iminoiodinanes as the nitrogen source, and substrate as the limiting reagent. Activated, benzylic, and aliphatic substrates can all be selectively functionalized in yields up to 87%. A mechanistic proposal for the observed reactivity supported by experimental evidence invokes the intermediacy of a diaziridinium salt or related organic nitrenoid, species that have not been previously explored for the purpose of C-H amination. Finally, examples of late-stage functionalization of complex molecules highlight the selectivity and potential utility of this catalytic method in synthesis.
- Combee, Logan A.,Raya, Balaram,Wang, Daoyong,Hilinski, Michael K.
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p. 935 - 939
(2018/02/07)
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- Catalytic asymmetric α-alkylation of ketones and aldehydes with N-benzylic sulfonamides through carbon-nitrogen bond cleavage
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A range of ketones and aldehydes smoothly undergo asymmetric SN1 α-alkylation with N-benzylic sulfonamides in the presence of 10 mol % of a chiral imidazolidinone and trifluoroacetic acid to give the corresponding products in good to excellent
- Weng, Zhen-Tao,Li, Yuan,Tian, Shi-Kai
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experimental part
p. 8095 - 8099
(2011/11/07)
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