Stereoselective syntheses of pinane-based 1,3-diamines and their application as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde

Efficient synthesis of α-alkyl-β-amino amides by transaminase-mediated dynamic kinetic resolutions

“…Also, -amino amides are synthetically useful precursors of valuable 1,3-diamines through reductive processes, and have been applied as ligands in metal-catalyzed reactions. 5 Among the different synthetic approaches (Fig. 2) that have been described to get access to enantio-or diastereoenriched β 3 -or β 2,3 -amino amides, the Mannich transformation has been the most applied.…”

Simple 1,3-diamines and their application as ligands in ruthenium(ii) catalysts for asymmetric transfer hydrogenation of aryl ketones

“…Some examples of symmetric 1,4-diamines and few examples of 1,3-diamines were reported in the literature, [12][13][14][15][16][17] mainly used as a typical ruthenium complex [(diphosphine)-RuCl 2 -(diamine)] for hydrogenation of simple aromatic and aliphatic ketones, in the catalytic addition of diethylzinc to aldehyde or in the Cu-catalyzed enantioselective Henry reaction. [18][19][20][21] Considering the wide range of 1,2-diamines used as ligands and their utility in asymmetric catalysis, this work reported the synthesis of simple asymmetric monotosylated 1,3-diamines, up to now poorly investigated in ATH (Fig. 1), and the evaluation of their catalytic performances.…”

Noscapine Derivatives as New Chiral Catalysts in Asymmetric Synthesis­: Highly Enantioselective Addition of Diethylzinc to Aldehydes­

“…In many reactions, amino alcohols are powerful catalysts. The majority of these are derived from natural compounds such as amino acids, 5 alkaloids, 6 or other natural scaffolds such as pinenes, 7 camphor, 8 etc. Catalysts with an alkaloidal backbone are among the most favorite organocatalysts because of their high efficiency in chiral induction.…”

“…C NMR (75 MHz, CDCl 3 ): δ = 142. 5,128.5,125.8,72.6,38.7,32.2,30.3,10.0. HRMS (ESI): m/z [M + Na] + calcd for C 11 H 16 ONa: 187.1099; found: 187.1097.…”