37746-17-1Relevant articles and documents
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Miller,R.G. et al.
, p. 4211 - 4220 (1974)
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Enantioselective Synthesis of N-Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(C6F5)3and a Chiral Lewis Acid Co-Catalyst
Chang, Yejin,Cao, Min,Chan, Jessica Z.,Zhao, Cunyuan,Wang, Yuankai,Yang, Rose,Wasa, Masayuki
supporting information, p. 2441 - 2455 (2021/02/16)
We disclose a catalytic method for β-C(sp3)-H functionalization of N-alkylamines for the synthesis of enantiomerically enriched β-substituted amines, entities prevalent in pharmaceutical compounds and used to generate different families of chiral catalysts. We demonstrate that a catalyst system comprising of seemingly competitive Lewis acids, B(C6F5)3, and a chiral Mg- or Sc-based complex, promotes the highly enantioselective union of N-alkylamines and α,β-unsaturated compounds. An array of δ-amino carbonyl compounds was synthesized under redox-neutral conditions by enantioselective reaction of a N-alkylamine-derived enamine and an electrophile activated by the chiral Lewis acid co-catalyst. The utility of the approach is highlighted by late-stage β-C-H functionalization of bioactive amines. Investigations in regard to the mechanistic nuances of the catalytic processes are described.
Iron-catalyzed oxidative C(3)-H functionalization of amines
Takasu, Noriaki,Oisaki, Kounosuke,Kanai, Motomu
, p. 1918 - 1921 (2013/06/04)
Fe-catalyzed direct dehydrogenative C(3)-functionalization of tertiary arylamines was developed via activation of the sp3 C(3)-H bond. The reaction is applicable to both cyclic and acyclic amines. The key process is the catalytic desaturative enamine formation from tertiary amines and position-selective C-C bond formation (addition to nitro olefins) at the β-carbon. Products can be converted to versatile and unique nitrogen-containing molecules.
Alkylsubstituted Cyclopentanones via Hydrocarbonylating Cyclization of 1,4-Pentadiene Systems Mediated by Metal Carbonyls
Eilbracht, Peter,Acker, Michael,Totzauer, Walter
, p. 238 - 242 (2007/10/02)
3,3-Dialkyl-1,4-pentadienes 8 under the influence of metal carbonyls can be converted to unsymmetrically substituted cyclopentanones 9 by hydrocarbonylating cyclization with carbon monoxide and hydrogen or water.Starting from 1,1-divinylcycloalkanes of type 8 this method can also be used for the synthesis of spirocyclopentanones.The yields of cyclic ketones with the here used dienes are markedly better than with the unsubstituted 1,4-pentadiene itself.
