128860-94-6Relevant articles and documents
Regio-and enantioselective catalytic monoepoxidation of conjugated dienes: Synthesis of chiral allylic cis-epoxides
Jat, Jawahar L.,De, Saroj Ranjan,Kumar, Ganesh,Adebesin, Adeniyi Michael,Gandham, Shyam K.,Falck, John R.
, p. 1058 - 1061 (2015)
Ti(IV)-salan 4 catalyzes the diastereo-and enantioselective monoepoxidation of conjugated dienes using 30% H2O2 at rt or below even in the presence of other olefins and adjacent stereocenters. Its enantiomer, ent-4, provides access to the opposite diastereomer or enantiomer. The resultant chiral allylic epoxides, and the triols derived from them, are versatile synthetic intermediates as well as substructures present in many bioactive natural products. The epoxidation is highly specific for Z-olefins. For 1-acyl(silyl)oxypenta-2,4-dienes, epoxidation of the distal olefin is generally favored in contrast to the adjacent regioselectivity characteristic of Sharpless, peracid, and other directed epoxidations of hydroxylated dienes.
SORBIC ACID IRON TRICARBONYL COMPLEX AS RESOLVING AGENT. CHIRAL SYNTHESES OF 4-HYDROXY NONENAL AND CORIOLIC ACID.
Montarby, Lucy de,Mosset, Paul,Gree, Rene
, p. 3937 - 3940 (2007/10/02)
The chiral iron tricarbonyl complex of sorbic acid 2 is an efficent resolving agent for allylic alcohol 3, which is a key intermediate in the preparation of most of the lipoxygenation products in n-6 position of polyunsaturated fatty acids.The synthesis of 4-hydroxy nonenal and methyl coriolate, in both enantiomeric forms, illustrates the potential of the method.