Synthesis of a new bridged diamine 3,6-diazabicyclo [3.2.0] heptane: Applications to the synthesis of quinolone antibacterials.

Iodomethylation of Chiral α-Amino Aldehydes by Means of Samarium/Diiodomethane. Application to the Synthesis of Various Enantiomerically Pure Compounds

“…21 The iodomethylation of amino aldehydes 1 with Sm/CH 2 I 2 took place with good diastereoselectivity. The diastereomeric excess (de) of compounds 4a-c was higher than 80%, as determined by 300-MHz 1 H NMR and quantitative 13 C NMR spectroscopy. Interestingly, when the reaction was carried out at lower temperature the de of 4b decreased (entry 5 in Table 1).…”

“…These compounds are important because of their biological properties and synthetic applications. As examples, chiral α-amino epoxides are highly useful intermediates in the synthesis of protease inhibitors and other pharmaceutically interesting compounds; the azetidine ring is present in an important number of molecules with biological activity; β-amino alcohols are biologically important, and the allylic amine moiety appears in many natural and bioactive compounds azetidines, and allylamines can be used as chiral building blocks for a wide variety of compounds, and β-amino alcohols can be used as chiral auxiliaries …”

“…These compounds are important because of their biological properties and synthetic applications. As examples, chiral R-amino epoxides are highly useful intermediates in the synthesis of protease inhibitors 11 and other pharmaceutically interesting compounds; 12 the azetidine ring is present in an important number of molecules with biological activity; 13 β-amino 102, 2693. (b) Tabuchi, T.; Inanaga, J.; Yamaguchi, J. Tetrahedron Lett.…”

ChemInform Abstract: Synthesis and Characterization of N‐Arylsulfonylazetidines.

“…Azetidines are valuable compounds in pharmaceutical research [1][2][3][4]. However, azetidines represent one of the more difficult group of amines to synthesize because of the unfavorable enthalpy of activation in four-membered ring formation [5].…”

Cationic ring-opening polymerization of N-phenylazetidine

“…Four-membered cyclic amines, i. e., azetidine and its derivatives, are known as a unique class of heterocyclic compounds [1,2] not only in pharmaceutical and biochemical research [3][4][5][6][7][8][9] but also in polymer chemistry [10,11] due to their potential ring-opening reactivity against appropriate nucleophiles in the presence of acids or alkylating reagents. Preceding studies on the polymerization of a variety of azetidines and N-alkylazetidines have revealed that the polymerization of azetidines proceeds via the initial formation of a quaternary cyclic ammonium (azetidinium) salt, followed by the propagation through the nucleophilic attack on this active species by an azetidine monomer.…”