Rapid and Efficient Access to Meso-2,5-cis-disubstituted Pyrrolidines by Double Aza-Michael Reactions of Chiral Primary Amines

Heterocycles ◽  
2007 ◽  
Vol 73 (1) ◽  
pp. 751 ◽  
Author(s):  
Delphine Joseph ◽  
Leila Cabral dos Santos ◽  
Zineb Bahlaouan ◽  
Khadija El Kassimi ◽  
Claire Troufflard ◽  
...  
Keyword(s):  
Primary Amines ◽  
Michael Reactions ◽  
Efficient Access

ChemInform Abstract: Rapid and Efficient Access to meso-2,5-cis-Disubstituted Pyrrolidines by Double Aza-Michael Reactions of Chiral Primary Amines.

ChemInform ◽  
2008 ◽  
Vol 39 (19) ◽  
Author(s):  
Leila Cabral dos Santos ◽  
Zineb Bahlaouan ◽  
Khadija El Kassimi ◽  
Claire Troufflard ◽  
Frederic Hendra ◽  
...  
Keyword(s):  
Primary Amines ◽  
Michael Reactions ◽  
Efficient Access

Domino Heck−Aza-Michael Reactions: Efficient Access to 1-Substituted Tetrahydro-β-carbolines

2010 ◽  
Vol 75 (5) ◽  
pp. 1787-1790 ◽  
Author(s):  
Daniel L. Priebbenow ◽  
Luke C. Henderson ◽  
Frederick M. Pfeffer ◽  
Scott G. Stewart
Keyword(s):  
Michael Reactions ◽  
Efficient Access

scholarly journals Efficient access to unprotected primary amines by iron-catalyzed aminochlorination of alkenes

Science ◽  
2018 ◽  
Vol 362 (6413) ◽  
pp. 434-439 ◽  
Author(s):  
Luca Legnani ◽  
Gabriele Prina-Cerai ◽  
Tristan Delcaillau ◽  
Suzanne Willems ◽  
Bill Morandi
Keyword(s):  
Room Temperature ◽  
Biologically Active ◽  
Primary Amines ◽  
General Strategy ◽  
Hydroxylamine Derivative ◽  
Homoallylic Amines ◽  
Efficient Access ◽  
Reaction Proceeds ◽  
Large Scope ◽  
Amphoteric Molecules

Primary amines are essential constituents of biologically active molecules and versatile intermediates in the synthesis of drugs and agrochemicals. However, their preparation from easily accessible alkenes remains challenging. Here, we report a general strategy to access primary amines from alkenes through an operationally simple iron-catalyzed aminochlorination reaction. A stable hydroxylamine derivative and benign sodium chloride act as the respective nitrogen and chlorine sources. The reaction proceeds at room temperature under air; tolerates a large scope of aliphatic and conjugated alkenes, including densely functionalized substrates; and provides excellent anti-Markovnikov regioselectivity with respect to the amino group. The reactivity of the 2-chloroalkylamine products, an understudied class of amphoteric molecules, enables facile access to linear or branched aliphatic amines, aziridines, aminonitriles, azido amines, and homoallylic amines.

ChemInform Abstract: Domino Heck-Aza-Michael Reactions: Efficient Access to 1-Substituted Tetrahydro-β-carbolines.

ChemInform ◽  
2010 ◽  
Vol 41 (25) ◽  
pp. no-no
Author(s):  
Daniel L. Priebbenow ◽  
Luke C. Henderson ◽  
Frederick M. Pfeffer ◽  
Scott G. Stewart
Keyword(s):  
Michael Reactions ◽  
Efficient Access

Step-Efficient Access to Chiral Primary Amines

Synthesis ◽  
2013 ◽  
Vol 45 (02) ◽  
pp. 153-166 ◽  
Author(s):  
Thomas Nugent ◽  
Sofiya Marinova
Keyword(s):  
Primary Amines ◽  
Efficient Access

Dielectric study of primary amines from room temperature down to −180 °C and from 10 kHz up to 35 GHz

1999 ◽  
Vol 8 (3) ◽  
pp. 241-246
Author(s):  
J. M. Forniés-Marquina ◽  
A. Siblini ◽  
L. Jorat ◽  
G. Noyel
Keyword(s):  
Room Temperature ◽  
Primary Amines ◽  
Dielectric Study

Acceptorless amine dehydrogenation and transamination using Pd-doped layered double hydroxides

2018 ◽  
Author(s):  
Diana Ainembabazi ◽  
Nan An ◽  
Jinesh Manayil ◽  
Kare Wilson ◽  
Adam Lee ◽  
...  
Keyword(s):  
Layered Double Hydroxides ◽  
Oxidation States ◽  
Secondary Amines ◽  
Primary Amines ◽  
Acid Dissolution ◽  
Oxidative Amination ◽  
Strong Function ◽  
Excellent Activity ◽  
High Yields ◽  
Double Hydroxides

<div> <p>The synthesis, characterization, and activity of Pd-doped layered double hydroxides (Pd-LDHs) for for acceptorless amine dehydrogenation is reported. These multifunctional catalysts comprise Brønsted basic and Lewis acidic surface sites that stabilize Pd species in 0, 2+, and 4+ oxidation states. Pd speciation and corresponding cataytic performance is a strong function of metal loading. Excellent activity is observed for the oxidative transamination of primary amines and acceptorless dehydrogenation of secondary amines to secondary imines using a low Pd loading (0.5 mol%), without the need for oxidants. N-heterocycles, such as indoline, 1,2,3,4-tetrahydroquinoline, and piperidine, are dehydrogenated to the corresponding aromatics with high yields. The relative yields of secondary imines are proportional to the calculated free energy of reaction, while yields for oxidative amination correlate with the electrophilicity of primary imine intermediates. Reversible amine dehydrogenation and imine hydrogenation determine the relative imine:amine selectivity. Poisoning tests evidence that Pd-LDHs operate heterogeneously, with negligible metal leaching; catalysts can be regenerated by acid dissolution and re-precipitation.</p> </div> <br>

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