The endo-aza-Michael addition in the synthesis of piperidines and pyrrolidines

Abstract

Intramolecular endo-aza-Michael additions are categorised in various ways.

DBU-catalyzed Michael addition of bulky glycine imine to α,β-unsaturated isoxazoles and pyrazolamides

“…bond formations [1][2][3][4][5]. Metal or metal-free catalyzed Michael additions have been well documented by many chemists [6][7][8][9][10]. The activated methylene compounds such as 1,3-dicarbonyl compounds, α-nitro-and α-cyanoesters are the most common Michael donors and used as pronucleophiles to attack electron-deficient alkenes in the presence of suitable catalysts [11][12][13][14][15][16].…”

Modelling of an aza-Michael reaction from crystalline naphthalene derivatives containing peri–peri interactions: very long N–C bonds?

“…3 The aza-Michael reaction, in particular, is used in the construction of heterocycles, alkaloids and molecules of pharmaceutical relevance. 4 Some calculations of the transition states structures and/or energies for such reactions have been reported, in some cases aimed at predicting mutagenicity of the Michael acceptor. 5,6 The idea of modelling reaction pathways based on structural data from crystals is well established for both organic and some inorganic systems though the experimental data generally lies closer to the start or end of the reaction process.…”

Regioselective Asymmetric Alkynylation of N-Alkyl Pyridiniums

“…Alkaloid natural products have a rich history in medicine, , thus fortuitously inspiring innovation and invention by synthetic chemists for decades . In turn, the piperidine heterocycle, a common moiety in bioactive alkaloids and rationally designed drugs, has demanded creative new strategies for its construction for many years. − Moreover, the asymmetric construction of substituted congeners of this important heterocycle has been of utmost importance in the synthetic pursuit of complex and medicinally relevant molecular targets …”