Gabriel-Cromwell aziridination of amino sugars; chiral ferrocenoyl-aziridinyl sugar synthesis and their biological evaluation.

N-sugar substituted chiral aziridines were synthesized via Gabriel-Cromwell reaction. Novel pure diastereomers of aziridine derivatives (4 diastereomers) were readily obtained in high yields and their structures were confirmed by means of H NMR, C NMR, FT-IR, Mass and optical rotations. This is, to the best of our knowledge, the unique example of N-sugar aziridine synthesis.

Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone.

A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, H NMR, C NMR, FT-IR, HRMS, optical rotation, and melting points. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. The compounds 9, 11 and 12 showed better activities at 25 μM against PC3 cell line with respect to the standard 5-fluorouracil (5-FU).

Pyrolysis of table sugar.

Table sugars were pyrolyzed at different temperatures (300, 400, and 500°C) in a fixed-bed reactor. The effect of pyrolysis temperature on yields of liquid, solid, and gaseous products was investigated. As expected the yield of liquid products gradually increased and the yield of solid products gradually decreased when the pyrolysis temperature was raised.

Catalytic asymmetric nitroaldol (Henry) reaction with a zinc-Fam catalyst.

Ferrocenyl-substituted aziridinylmethanol (Fam-1) was used as a catalyst with zinc for the asymmetric nitroaldol (Henry) reaction. This catalyst worked with a variety of aldehydes (aromatic, aliphatic, alpha,beta-unsaturated, and heteroaromatic) and alpha-ketoesters to give the nitroaldol product in up to 97% yield and 91% ee. The chiral ligand can be recovered and recycled without losing its activity.

1,4-Diferrocenylbutane-1,4-dione.

In the crystal structure of the title compound, [Fe(2)(C(5)H(5))(2)(C(14)H(12)O(2))], each carbonyl group is coplanar with the adjacent cyclo-penta-dienyl ring, thus maximizing the π-orbital overlap and electronic inter-actions between the groups. In the crystal structure, there are inter- and intra-molecular C-H⋯O contacts.

New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions.

[reaction: see text] A new chiral aziridino alcohol ligand for zinc(II)-catalyzed azomethine ylide cycloadditions is described. In the presence of this catalyst, N-arylidene glycine methyl esters react with a variety of dipolarophiles to give substituted pyrrolidines in very good to excellent chemical yields and up to 95% ee. The absolute sense of asymmetric induction appears to be dipolarophile-dependent.