Nucleophilic Addition to Imines and Imine Derivatives

Aza‐Henry Reactions of 3,4‐Dihydroisoquinoline

“…The literature contains numerous examples of the reaction of imines with organometallic reagents, [6] or the reaction of alkylated or acylated (Reissert-like) isoquinolines with (frequently reactive, metallated) nucleophiles (5 to 6, see Scheme 1,B). [7][8][9] Recent examples of the reaction of isoquinolines with non-organometallic species include Shibasaki's catalytic, asymmetric cyanation of isoquinolines, [10] Jorgensen's intramolecular organocatalytic annulation reaction of an enamine with an alkyliminium ion in the synthesis of 1,2-dihydroisoquinoline derivatives, [11] and Jacobsen's organocatalyzed acyl nitro-Mannich reaction between isoquinolines and silyl ketene acetals. [12,13] Reports of similar reactions with dihydroisoquinolines rather than quinolines are fewer in number, but, besides the synthesis of Reisserttype compounds, [14] include intramolecular [15] and intermolecular [16] attack of enolates on alkyldihydroisoquinolinium salts, enolate addition to a chiral acyldihydroisoquinolinium salt, [17] enantioselective metal-catalyzed addition of malonates and alkenylzirconocenes to acyldihydroisoquinolinium salts, [18] and 1,3-dipolar cycloadditions of the azomethine ylides derived from Reissert compounds.…”

Direct synthesis of amides and imines by dehydrogenative homo or cross-coupling of amines and alcohols catalyzed by Cu-MOF

“…Imines are of great importance for the synthesis of chemical and biologically active compounds such as amines, chiral amines, amides, pyrrolines, hydroxyamines, and oxaziridines. [1][2][3] Typically for the synthesis of imines, a mixture of an aldehyde or ketone with an amine in the presence of a catalyst is required. On the other hand, many useful oxidation methods for the synthesis of imines have been developed 4 which include dimerization of primary amines [5][6][7][8][9][10] oxidation of secondary amines [11][12][13][14] and other methodologies.…”

Efficient Solvent-Free Preparation of Imines, and Their Subsequent Oxidation with <i>m</i>-CPBA to Afford Oxaziridines

“…On the other hand, imines are useful intermediates in organic synthesis, acting as electrophilic reagents in many synthetic transformations, including addi-tions, condensations, and cycloadditions. Thus, the development of an easy synthetic protocol for the preparation of imines is highly desirable [16] [17] [18].…”