BF3·OEt2-Promoted Diastereoselective Diacetoxylation of Alkenes by PhI(OAc)2
- 17 November 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 76 (24), 9997-10004
- https://doi.org/10.1021/jo201752y
Abstract
Selective syn and anti diacetoxylations of alkenes have been achieved using a PhI(OAc)2/BF3·OEt2 system in the presence and absence of water, respectively. A broad range of substrates including electron-deficient alkenes (such as α,β-unsaturated esters) could be elaborated efficiently at room temperature with this methodology, furnishing the desired products in good to excellent yields and diastereoselectivity. In particular, a multigram-scale diastereoselective diacetoxylation of methyl cinnamate (5.00 g) was also accomplished in a few hours, maintaining the same efficiency as small-scale reaction. This novel methodology provides an alternative approach for the preparation of various 1,2-diols.Keywords
This publication has 59 references indexed in Scilit:
- A Novel Platform for Modeling Oxidative Catalysis in Non‐Heme Iron Oxygenases with Unprecedented EfficiencyChemistry – A European Journal, 2008
- Catalytic Epoxidation and syn-Dihydroxylation Reactions in Steroid ChemistryCurrent Organic Chemistry, 2008
- Iron‐Catalyzed Asymmetric Olefin cis‐Dihydroxylation with 97 % Enantiomeric ExcessAngewandte Chemie-International Edition, 2008
- Iron(II) Complexes with Bio‐Inspired N,N,O Ligands as Oxidation Catalysts: Olefin Epoxidation and cis‐DihydroxylationChemistry – A European Journal, 2008
- Catalytic Asymmetric DihydroxylationChemical Reviews, 1994
- Selective Perhydroxylation of Squalene: Taming the Arithmetic DemonScience, 1993
- Mechanism of asymmetric epoxidation. 2. Catalyst structureJournal of the American Chemical Society, 1991
- Asymmetric dihydroxylation via ligand-accelerated catalysisJournal of the American Chemical Society, 1988
- Osmium tetraoxide cis hydroxylation of unsaturated substratesChemical Reviews, 1980
- An improved catalytic OsO4 oxidation of olefins to -1,2-glycols using tertiary amine oxides as the oxidantTetrahedron Letters, 1976