Regio- and stereoselective monoepoxidation of dienes using methyltrioxorhenium: Synthesis of allylic epoxides

Saroj Ranjan De, Ganesh Kumar, Jawahar L. Jat, Saritha Birudaraju, Biao Lu, Rajkumar Manne, Narender Puli, Adeniyi Michael Adebesin, J R Falck

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

Methyltrioxorhenium (MTO) complexed with pyridine was shown to be a highly effective catalyst for the regioselective monoepoxidation of conjugated di- and trienes using 30% H2O2 at or below room temperature. The resultant allylic epoxides, and the triols derived from them, are versatile synthetic intermediates as well as substructures present in many bioactive natural products. The site of epoxidation was dependent upon olefin substitution, olefin geometry (Z vs E), and the presence of electron-withdrawing substituents on adjacent carbons. For 1-acyl(silyl)oxypenta-2,4-dienes, epoxidation of the distal olefin was 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)10323-10333
Number of pages11
JournalJournal of Organic Chemistry
Volume79
Issue number21
DOIs
StatePublished - Nov 7 2014

ASJC Scopus subject areas

  • Organic Chemistry

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    De, S. R., Kumar, G., Jat, J. L., Birudaraju, S., Lu, B., Manne, R., Puli, N., Adebesin, A. M., & Falck, J. R. (2014). Regio- and stereoselective monoepoxidation of dienes using methyltrioxorhenium: Synthesis of allylic epoxides. Journal of Organic Chemistry, 79(21), 10323-10333. https://doi.org/10.1021/jo501958d