582-22-9Relevant articles and documents
CO2-Assisted asymmetric hydrogenation of prochiral allylamines
Alridge, Christopher J.,De Winter, Tamara M.,Ho, Jaddie,Jessop, Philip G.
, p. 6755 - 6761 (2022/03/31)
A new methodology for the asymmetric hydrogenation of allylamines takes advantage of a reversible reaction between amines and carbon dioxide (CO2) to suppress unwanted side reactions. The effects of various parameters (pressure, time, solvent, and base additives) on the enantioselectivity and conversion of the reaction were studied. The homogeneously-catalyzed asymmetric hydrogenation of 2-arylprop- 2-en-1-amine resulted in complete conversion and up to 82% enantiomeric excess (ee). Added base, if chosen carefully, improves the enantioselectivity and chemoselectivity of the overall reaction.
Iron-Catalyzed Diastereoselective Synthesis of Disubstituted Morpholines via C-O or C-N Bond Formation
Aubineau, Thomas,Dupas, Alexandre,Zeng, Tian,Cossy, Janine
supporting information, p. 525 - 531 (2020/08/28)
The diastereoselective synthesis of 2,6- and 3,5-disubstituted morpholines was achieved from 1,2-amino ethers and 1,2-hydroxy amines substituted by an allylic alcohol using an iron(III) catalyst. The morpholines were obtained either by C-O or C-N bond formation. A plausible mechanism is suggested, involving a thermodynamic equilibrium to explain the formation of the cis diastereoisomer as the major product.
Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines
Cabré, Albert,Verdaguer, Xavier,Riera, Antoni
, p. 4196 - 4200 (2019/08/16)
The iridium-catalyzed asymmetric hydrogenation of several N-sulfonyl allyl amines is reported. All substrates can be easily obtained by the Ir-catalyzed isomerization of N-tosylaziridines reported previously. The commercially available threonine-derived phosphinite (UbaPHOX) iridium complex has been found to be the best catalyst for this catalytic application, affording β-methyl amines with good to excellent ee values (up to 94%). The synthetic potential of this novel methodology was demonstrated by the formal synthesis of Lorcaserin and LY-404187. (Figure presented.).