6560-75-4Relevant academic research and scientific papers
A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles
Armstrong, Roly J.,Chamberlain, Anna E. R.,Donohoe, Timothy J.,Paterson, Kieran J.,Twin, Heather C.
supporting information, p. 3563 - 3566 (2020/04/03)
An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiopure diols could undergo annulation with minimal racemization, enabling the synthesis of valuable enantioenriched C3 and C4-substituted saturated aza-heterocycles.
Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines
Musacchio, Andrew J.,Lainhart, Brendan C.,Zhang, Xin,Naguib, Saeed G.,Sherwood, Trevor C.,Knowles, Robert R.
, p. 727 - 730 (2017/02/26)
The intermolecular hydroamination of unactivated alkenes with simple dialkyl amines remains an unsolved problem in organic synthesis. We report a catalytic protocol for efficient additions of cyclic and acyclic secondary alkyl amines to a wide range of alkyl olefins with complete anti-Markovnikov regioselectivity. In this process, carbon-nitrogen bond formation proceeds through a key aminium radical cation intermediate that is generated via electron transfer between an excited-state iridium photocatalyst and an amine substrate. These reactions are redox-neutral and completely atom-economical, exhibit broad functional group tolerance, and occur readily at room temperature under visible light irradiation. Certain tertiary amine products generated through this method are formally endergonic relative to their constituent olefin and amine starting materials and thus are not accessible via direct coupling with conventional ground-state catalysts.
Tandem polar/radical crossover sequences for the formation of fused and bridged bicyclic nitrogen heterocycles involving radical ionic chain reactions, and alkene radical cation intermediates, performed under reducing conditions: Scope and limitations
Crich, David,Ranganathan, Krishnakumar,Neelamkavil, Santhosh,Huang, Xianhai
, p. 7942 - 7947 (2007/10/03)
It is demonstrated that phosphorylated forms of β-nitro alcohols provide an excellent means of entry into β-(phosphatoxy)alkyl radicals on exposure to tributyltin hydride and AIBN in benzene at reflux. These radicals then undergo heterolytic cleavage of t
Generation and trapping of alkene radical cations under nonoxidizing conditions: Formation of six-membered rings by exo- and endo-mode cyclizations
Crich, David,Neelamkavil, Santhosh
, p. 2573 - 2575 (2007/10/03)
(Matrix presented) It is demonstrated that alkene radical cations generated by the radical ionic fragmentation of β-(phosphatoxy)alkyl radicals undergo efficient nucleophilic capture by amines in either the 6-exo or 6-endo modes, leading to six-membered n
Syntheses of nitrogen heterocycles by means of amine-directed carbonylation and hydrocarbonylation
Zhang, Zhaoda,Ojima, Iwao
, p. 281 - 289 (2007/10/02)
Amine-directed carbonylation of 2-allylpiperidine (5) gives 8-methyl-1-azabicyclononan-9-one (7) with extremely high regio- and stereoselectivity, which is promoted by a stoichiometric amount of 2 in the presence of hydrogen chloride.A c
