Regio-and enantioselective catalytic monoepoxidation of conjugated dienes: Synthesis of chiral allylic cis-epoxides

Jawahar L. Jat, Saroj Ranjan De, Ganesh Kumar, Adeniyi Michael Adebesin, Shyam K. Gandham, J R Falck

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)1058-1061
Number of pages4
JournalOrganic Letters
Volume17
Issue number4
DOIs
StatePublished - Feb 20 2015

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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