Regio- and Enantioselective Catalytic Monoepoxidation of Conjugated Dienes: Synthesis of Chiral Allylic cis-Epoxides

• Published in: Organic letters Vol. 17; no. 4; pp. 1058 - 1061
• Main Authors: Jat, Jawahar L, De, Saroj Ranjan, Kumar, Ganesh, Adebesin, Adeniyi Michael, Gandham, Shyam K, Falck, John R
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.02.2015; Amer Chemical Soc
• Subjects: Alkadienes - chemical synthesis; Alkadienes - chemistry; Biological Products - chemistry; Catalysis; Chemistry; Chemistry, Organic; Combinatorial Chemistry Techniques; Epoxy Compounds - chemical synthesis; Epoxy Compounds - chemistry; Hydrogen Peroxide - chemistry; Letter; Molecular Structure; Physical Sciences; Science & Technology; Stereoisomerism; DIHYDROXYLATION; EPOXY ALCOHOLS; AQUEOUS HYDROGEN-PEROXIDE; COMPLEXES; ASYMMETRIC EPOXIDATION; SHARPLESS EPOXIDATION; HYDROPEROXIDE; OLEFINS; FATTY-ACIDS; ARACHIDONIC-ACID

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 a...