3728-50-5Relevant articles and documents
THE ENANTIOSPECIFIC SYNTHESIS OF (4S,5R)-AND (4S,5S)-4,5-DIHYDROXYDECANOIC ACID γ-LACTONES, PROPOSED AUTOREGULATORS FROM STREPTOMYCES GRISEUS
Cooper, Roderick D.,Jigajinni, Veerappa B.,Wightman, Richard H.
, p. 5215 - 5218 (1984)
Both the (4S,5R)- and (4S,5S)-isomers of 4,5-dihydroxydecanoic acid γ-lactone, natural products and proposed autoregulators of Streptomyces Griseus, have been synthesised directly and in high yield from D-ribose via a common intermediate.
A versatile protocol for the quantitative and smooth conversion of phosphane oxides into synthetically useful pyrazolylphosphonium salts
Feldmann, Kai-Oliver,Schulz, Stephen,Klotter, Felix,Weigand, Jan J.
, p. 1805 - 1812 (2012/04/04)
A convenient protocol for the smooth conversion of the resistant P-O bond in phosphane oxides into a reactive P-N bond of synthetically useful pyrazolylphosphonium salts is described. A highly charged, oxophilic, phosphorus-centered trication is employed and the reactions are conducted at room temperature with quantitative yields. The resulting pyrazolylphosphonium cations are valuable synthetic intermediates and are used for the synthesis of a variety of organophosphorus compounds. This represents a new approach towards the transformation of the rather inert phosphoryl group under very mild reaction and workup conditions and aims towards alternatives to existing reduction methods for phosphane oxide functionalization.
Untersuchungen im Wittig-System nach einem ordnenden Konzept auf der Basis alternativer Prinzipien
Bandmann, Heinz,Bartik, Tamas,Bauckloh, Sylvia,Behler, Ansgar,Brille, Frank,et al.
, p. 193 - 204 (2007/10/02)
Our results show that the stereoselectivity of the Wittig-reaction can be controlled by the variation of substituents in accord with the ORDERING CONCEPT OF ALTERNATIV PRINCIPLES (individual pairs, known and unknown classes of alternatives).The "all-phenyl Wittig-system" having three phenyl groups on phosphorous two in ylid- and aldehyd-position was chosen as a standard for our investigations.Differentiation in ylid-position and compensation on phosphorous and aldehyd-position were observed by the comparison of "patterns".Consequently, most of the selectivity rules of Wittig-reactions can be explained by the differentiation through alternatives in the ylid-position.Inversion or conservation of the "patterns" of measured data points to the variation in structure of starting materials, reaction rates and selectivities.Amount-controls were also described in certain systems.