Journal article

Publication year: 2019

Pages: 12377-12386

Journal: The Journal of Organic Chemistry

Volume number: 84

Issue number: 19

ISSN: 0022-3263

DOI Link: https://doi.org/10.1021/acs.joc.9b01748

Publisher: American Chemical Society

Abstract: 
The syn-dihydroxylation of alkenes is a highly valuable reaction in organic synthesis. Cyclic acyl peroxides (CAPs) have emerged recently as promising candidates to replace the commonly employed toxic metals for this purpose. Here, we demonstrate that the structurally demanding cyclic peroxide spiro[bicyclo[2.2.1]heptane-2,4 '-[1,2]dioxolane]-3 ',5 '-dione (P4) can be effectively used for the syn-dihydroxylation of alkenes. Reagent P4 also shows an improved selectivity for dihydroxylation of alkenes bearing beta-hydrogens as compared to other CAPs, where both diol and allyl alcohol products compete with each other. Furthermore, the use of enantiopure P4 (labeled P4 ') demonstrates the potential of P4 ' for a metal-free asymmetric syn-dihydroxylation of alkenes.

Harvard Citation style: Pilevar, A., Hossein, A., Becker, J. and Schreiner, P. (2019) Syn-Dihydroxylation of Alkenes Using a Sterically Demanding Cyclic Diacyl Peroxide, The Journal of Organic Chemistry, 84(19), pp. 12377-12386. https://doi.org/10.1021/acs.joc.9b01748

APA Citation style: Pilevar, A., Hossein, A., Becker, J., & Schreiner, P. (2019). Syn-Dihydroxylation of Alkenes Using a Sterically Demanding Cyclic Diacyl Peroxide. The Journal of Organic Chemistry. 84(19), 12377-12386. https://doi.org/10.1021/acs.joc.9b01748