C?C-Bond Formation in the ?-Position to Nitrogen in Secondary Amines. Lithiodimethylnitrosamine

1972 ◽  
Vol 11 (4) ◽  
pp. 301-302 ◽  
Author(s):  
Dieter Seebach ◽  
Dieter Enders
Keyword(s):  
Bond Formation ◽  
Secondary Amines

scholarly journals Kinetic resolution of indolines by asymmetric hydroxylamine formation

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Gang Wang ◽  
Ran Lu ◽  
Chuangchuang He ◽  
Lei Liu
Keyword(s):  
Hydrogen Peroxide ◽  
Chemical Synthesis ◽  
Late Stage ◽  
Kinetic Resolution ◽  
High Efficiency ◽  
Bond Formation ◽  
Bioactive Molecules ◽  
Environmentally Benign ◽  
Secondary Amines

AbstractCatalytic kinetic resolution of amines represents a longstanding challenge in chemical synthesis. Here, we described a kinetic resolution of secondary amines through oxygenation to produce enantiopure hydroxylamines involving N–O bond formation. The economic and practical titanium-catalyzed asymmetric oxygenation with environmentally benign hydrogen peroxide as oxidant is applicable to a range of racemic indolines with multiple stereocenters and diverse substituent patterns in high efficiency with efficient chemoselectivity and enantio-discrimination. Late-stage asymmetric oxygenation of bioactive molecules that are otherwise difficult to synthesize was also explored.

Catalyst free C–N bond formation by the reaction of amines with diimides: bulky guanidines

2015 ◽  
Vol 39 (9) ◽  
pp. 7503-7510 ◽  
Author(s):  
Ashim Baishya ◽  
Thota Peddarao ◽  
Milan Kr. Barman ◽  
Sharanappa Nembenna
Keyword(s):  
Bond Formation ◽  
Secondary Amines ◽  
Catalyst Free ◽  
Direct Addition

Catalyst free direct addition of cyclic secondary amines to various N,N′-bisaryl substituted carbodiimides led to the formation of bulky guanidines. Furthermore, two equivalents of N,N′-bisaryl substituted carbodiimides upon treatment with piperazine led to the formation of bis guanidines.

Carbon–Carbon Bond Formation via Catalytically Generated Aminocarbene Complexes: Rhodium‐Catalyzed Hydroaminative Cyclization of Enynes with Secondary Amines

2020 ◽  
Vol 132 (29) ◽  
pp. 11852-11855
Author(s):  
Shotaro Takano ◽  
Ryosuke Shiomi ◽  
Yoshihiko Morimoto ◽  
Takuya Kochi ◽  
Fumitoshi Kakiuchi
Keyword(s):  
Bond Formation ◽  
Secondary Amines ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Carbon–Carbon Bond Formation via Catalytically Generated Aminocarbene Complexes: Rhodium‐Catalyzed Hydroaminative Cyclization of Enynes with Secondary Amines

2020 ◽  
Vol 59 (29) ◽  
pp. 11754-11757
Author(s):  
Shotaro Takano ◽  
Ryosuke Shiomi ◽  
Yoshihiko Morimoto ◽  
Takuya Kochi ◽  
Fumitoshi Kakiuchi
Keyword(s):  
Bond Formation ◽  
Secondary Amines ◽  
Carbon Bond ◽  
Carbon Carbon Bond

scholarly journals A CO2-Catalyzed Transamidation Reaction

2020 ◽  
Author(s):  
Yang Yang ◽  
Jian Liu ◽  
JIWOONG LEE
Keyword(s):  
Transition State ◽  
Bond Formation ◽  
Metal Catalysts ◽  
Amide Bond ◽  
Secondary Amines ◽  
Coupling Reagents ◽  
Reaction Conditions ◽  
Amide Bond Formation ◽  
Primary And Secondary Amines ◽  
Bond Formation Reactions

<div> <div> <div> <p>Amide bond formation reactions are often mediated by reactive substrates in the presence of over-stoichiometric activating reagents and/or catalysts. Here we report a CO2-promoted transamidation reaction without additive metal catalysts or coupling reagents. The reaction forms byproducts, ammonia, primary and secondary amines, which can form adducts with CO2, thereby shifting the equilibrium in the desired direction. A comparison of Hammett studies under CO2 and N2 atmospheres suggests that the reaction transition state can be stabilized by electrophilic CO2. Selective modification of peptides was demonstrated, showing that CO2 can be utilized to control the nature of the electrophilicity and nucleophilicity of reaction partners under practical reaction conditions. </p> </div> </div> </div>

scholarly journals A CO2-Catalyzed Transamidation Reaction

2020 ◽  
Author(s):  
Yang Yang ◽  
Jian Liu ◽  
JIWOONG LEE
Keyword(s):  
Transition State ◽  
Bond Formation ◽  
Metal Catalysts ◽  
Amide Bond ◽  
Secondary Amines ◽  
Coupling Reagents ◽  
Reaction Conditions ◽  
Amide Bond Formation ◽  
Primary And Secondary Amines ◽  
Bond Formation Reactions

<div> <div> <div> <p>Amide bond formation reactions are often mediated by reactive substrates in the presence of over-stoichiometric activating reagents and/or catalysts. Here we report a CO2-promoted transamidation reaction without additive metal catalysts or coupling reagents. The reaction forms byproducts, ammonia, primary and secondary amines, which can form adducts with CO2, thereby shifting the equilibrium in the desired direction. A comparison of Hammett studies under CO2 and N2 atmospheres suggests that the reaction transition state can be stabilized by electrophilic CO2. Selective modification of peptides was demonstrated, showing that CO2 can be utilized to control the nature of the electrophilicity and nucleophilicity of reaction partners under practical reaction conditions. </p> </div> </div> </div>

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