Recent Developments in the Stereoselective Synthesis of Nitrogen‐Containing Heterocycles using N‐Acylimines as Reactive Substrates

Abstract

Scheme 3. Enantioselective synthesis of trans-aziridines 8 catalyzed by chiral phosphoric acid 10. Scheme 4. Enantioselective synthesis of trans-aziridines 14. Scheme5.Preparation of chiral aziridines 17. Scheme6.Synthesis of chiral aziridines 20. Scheme 22. Synthesis of chiral 2-pyrrolines 82. Scheme23. Enantioselective synthesis of epi-cytoxazone 89. Scheme 24. Synthesis of the mGluR5modulator 96. Scheme 25. Synthesis of chiral 1,3-oxazolines. Scheme26. Synthesis of chiral imidazolidin-2-one 102. Scheme 27. Enantioselectiven itro-Mannichr eaction.Scheme28. Synthesis of (À)-nutlin-3 111.Scheme29. Synthesis of functionalized tetrahydropyridines. Scheme 32. Synthesis of chiral piperidines 129. Scheme 33. One-pot synthesis of N-formylpiperidines. Scheme34. Synthesis of bicyclic aminal 136. Scheme 39. General synthesis of isatin ketimines. Scheme 40. Asymmetric Staudinger reaction. Scheme41. Synthesis of spirocyclic oxindolo-g-lactams. Scheme 42. Synthesis of methylidenes pirocyclic compounds. Scheme 43. Synthesis of spirooxindolepyrrolines. Scheme44. Synthesis of imidazoline-based spirooxindoles. Scheme 48. Synthesis of spirolactam derivatives. Scheme49. Synthesis of spirooxindolelactams 201. Scheme50. Synthesis of polycyclic spirolactams 203. Scheme 56. Synthesis of chiral spiroazetidin-2-ones 228.

Aldolase‐Catalyzed Asymmetric Synthesis of N‐Heterocycles by Addition of Simple Aliphatic Nucleophiles to Aminoaldehydes

“…The ring type, e. g. piperidine, pyrrolidine, pyrrolizidine, N‐bicyclics, and the structure, position and stereochemistry of the substituents, play a fundamental role in modulating their biological activity . Methods for the total synthesis of a broad structural diversity of N‐heterocycles, either as building blocks or as final compounds for biological testing, are thus in high demand . Although the number of chemical routes available to prepare these compounds is extensive, developing new stereoselective synthetic methodology is essential yet challenging …”

“…Methods for the total synthesis of a broad structural diversity of N‐heterocycles, either as building blocks or as final compounds for biological testing, are thus in high demand . Although the number of chemical routes available to prepare these compounds is extensive, developing new stereoselective synthetic methodology is essential yet challenging …”

Stereoselectivity of the Biginelli Reaction Catalyzed by Chiral Primary Amine: A Computational Study

“…One of the effective ways to form DHPMs is the Biginelli reaction, which is a three component one-pot reaction involving aldehyde, (thio)urea, and −keto ester. [2][3][4][5] Enantioselective Biginelli reactions have been carried out by a number of chiral metal complex catalysts, 6,7 and chiral organocatalysts, such as primary amines, 8,9 proline derivatives, [10][11][12] pyrrolidinyl tetrazoles, 13 pyrazolidine, 14 quinidine-based thiourea, 15 phosphoric acids, 16,17 bisphosphorylimide, 18 and nanocomposites. 19 Among them, primary amine with a chiral diamine backbone is one of the most efficient chiral catalysts.…”

Novel semicarbazone-based α-amidoalkylating reagents: general synthesis and reactions with <em>H</em>-, <em>O</em>-, <em>S</em>-, <em>N</em>-, and <em>P</em>-nucleophiles

“…Therefore, amidoalkylation has been extensively applied in the synthesis of various nitrogencontaining acyclic and heterocyclic compounds including bioactive natural products (e.g., alkaloids [4][5][6][7], antibiotics [8][9][10][11], toxins [12][13][14], vitamins [15,16]) and pharmaceuticals [17][18][19][20]. Recently, some enantioselective variants of this reaction employing catalytic amounts of chiral auxiliaries has also been described [21][22][23]. Scheme 1.…”