Highly efficient catalytic asymmetric epoxidation of allylic alcohols by an oxovanadium-substituted polyoxometalate with a regenerative TADDOL-derived hydroperoxide

Waldemar Adam; Paul L Alsters; Ronny Neumann; Chantu R Saha-Möller; Dieter Seebach; Rui Zhang

doi:10.1021/ol027498p

Highly efficient catalytic asymmetric epoxidation of allylic alcohols by an oxovanadium-substituted polyoxometalate with a regenerative TADDOL-derived hydroperoxide

Org Lett. 2003 Mar 6;5(5):725-8. doi: 10.1021/ol027498p.

Authors

Waldemar Adam¹, Paul L Alsters, Ronny Neumann, Chantu R Saha-Möller, Dieter Seebach, Rui Zhang

Affiliation

¹ Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany. [email protected]

PMID: 12605500
DOI: 10.1021/ol027498p

Abstract

The oxovanadium(IV) sandwich-type POM catalyzes the chemo-, regio-, and stereoselective epoxidation of allylic alcohols by chiral hydroperoxides with very high catalytic efficiency (up to 42 000 TON), a potentially valuable oxidation for the development of sustainable processes. By using the sterically demanding, TADDOL-derived hydroperoxide TADOOH as the chiral oxygen source, enantiomeric ratios (er) of up to 95:5 have been achieved.