Asymmetric 1,3-Dipolar Cycloadditions of Cyclic Stabilized Ylides Derived from Chiral 1,2-Amino Alcohols

Abstract

The use of structurally similar chiral non-racemic azomethine ylides, nitrones and azomethine imines derived from 1,2-aminol alcohols in asymmetric dipolar cycloadditions is reviewed. This general survey underlines the great synthetic potential of dipolar cycloadditions, especially in a diversity-oriented approach and enables a direct comparison of the reactivity of apparently closely related reactive systems.

Synthesis , Characterization and computional study of Some New Aniline oxide derivatives

“…(0.467mole) of ammonium chloride, 800 ml of water and the appropriate 5-(furan-2-yl)-3-(4nitrophenyl)-4,5-dihydro-1H-pyrazole (0.406 mole) (which was prepared as mention in the literature) (51) were placed in a three-neck round bottom flask. This mixture was stirred with a mechanical stirrer; and 59 g of zinc powder was added during (15)(16)(17)(18)(19)(20) minutes. As the reduction proceeded, the temperature rised to (60-65)°C, stirring was continued for 15minutes in which all the zinc powder was added, at the end of which the reaction was complete, as indicated by the lowering of the temperature of the reaction mixture.…”

(5R)-3-(2-Chloroacetyl)-4-methyl-5-phenyl-1,3,4-oxadiazinan-2-one

“…For background to 1,3,4-oxadiazin-2-ones, see: Trepanier et al (1968); Roussi et al (1998Roussi et al ( , 1999Roussi et al ( , 2000; Casper et al (2002a,b); Bonin et al (2006). For a related structure, see: Zukerman-Schpector et al (2009).…”

“…About forty years ago Trepanier and collaborators reported the first synthesis of some 3,4,5,6-tetrahydro-2H-1,3,4oxadiazin-2-ones as candidates for central nervous system stimulant activity (Trepanier et al, 1968). After three decades from the discovery of 1,3,4-oxadiazin-2-ones, Husson, Micouin and co-workers (Roussi et al, 1998) successfully employed this class of compound as chiral auxiliaries in diastereoselective alkylations and in dipolar cycloadditions (Roussi et al, 1999, 2000, Bonin et al, 2006. In a different approach, Hitchcock and collaborators have been successfully applying 1,3,4-oxadiazinan-2-one derivatives as chiral auxiliaries in asymmetric aldol addition reactions (Casper et al, 2002b).…”

Efficient Synthesis of Isoxazolidine-Tethered Monolayer-Protected Gold Nanoparticles (MPGNs) via 1,3-Dipolar Cycloadditions under High-Pressure Conditions

“…While the bulk of the attention directed toward this reaction has centered about the Diels−Alder reaction, other cycloadditions have established their place in the toolbox of the synthetic chemist. 1,3-Dipolar cycloadditions, for example, are some of the most useful ways to construct heterocyclic rings . Often, simple variation of the dipolar or dipolarophilic partners offers a method for incorporation of a large degree of structural diversity.…”