14440-50-7Relevant articles and documents
Synthesis and reactivity of nonstabilized diazo sugars
Alexander, Michael S.,Horton, Derek
, p. 31 - 43 (2007)
1,6-Anhydro-4-deoxy-4-diazo-2,3-O-isopropylidene-β-d-lyxo-hexopyranose (4) is a stable crystalline compound readily accessible by an improved synthetic procedure. It has been used as a model for evaluating the reactivity of the diazo group, when not stabilized by an adjacent carbonyl function, in a rigid chiral matrix. A range of carbene-type, electrophile-promoted, and 1,3-dipolar reactions were evaluated, leading to 4,4′-alkene dimers, 4-deoxy-3-enose and related derivatives, 4,4-dihalo compounds, 4-spirocyclopropane derivatives, 4-spiropyrazole structures, and by skeletal rearrangement, branched-chain anhydropentose structures having a bicyclo[2.2.2] skeleton.
Intra- and intermolecular 1,3-dipolar cycloaddition of sugar ketonitrones with mono-, di-, and trisubstituted dipolarophiles
Torrente, Susana,Noya, Beatriz,Branchadell, Vicenc,Alonso, Ricardo
, p. 4772 - 4783 (2007/10/03)
The 1,3-dipolar cycloaddition of sugar ketonitrones is a useful synthetic procedure to build up nitrogenated quaternary centers in terms of scope (substrate, dipolarophile, inter- and intramolecular versions), yield, and regio- and stereoselectivity. The
Structural probing of ketone catalysts for asymmetric epoxidation
Tu, Yong,Wang, Zhi-Xian,Frohn, Michael,He, Mingqi,Yu, Hongwu,Tang, Yong,Shi, Yian
, p. 8475 - 8485 (2007/10/03)
A series of chiral ketones derived from carbohydrates were investigated as catalysts for the asymmetric epoxidation. Fructose-derived ketones are found to be efficient catalysts. The studies show that the structural requirements for the ketone catalysts are very stringent and different types of olefins may require ketones with different structural arrangements. The current study allows us to further understand the chiral ketone catalyzed asymmetric epoxidation and provides some insight for the development of new catalysts.