Stereoselective Radical Azidooxygenation of Alkenes
- 9 August 2013
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 15 (17), 4548-4551
- https://doi.org/10.1021/ol402106x
Abstract
Radical azidooxygenation of various alkenes is described. A readily prepared N3-iodine(III) reagent acts as a clean N3-radical precursor. Radical generation is achieved with TEMPONa acting as a mild organic reducing reagent. The C-radical generated after N3-radical addition is efficiently trapped by in situ generated TEMPO. Yields are good to excellent, and for cyclic systems azidooxygenation occurs with excellent diastereoselectivity.Keywords
This publication has 52 references indexed in Scilit:
- Radical azidation reactions and their application in the synthesis of alkaloidsPure and Applied Chemistry, 2012
- Iron(III)/NaBH4-Mediated Additions to Unactivated Alkenes: Synthesis of Novel 20′-Vinblastine AnaloguesOrganic Letters, 2012
- “Clicking” Polymers or Just Efficient Linking: What Is the Difference?Angewandte Chemie, 2010
- Cobalt-Catalyzed Hydroazidation of Olefins: Convenient Access to Alkyl AzidesJournal of the American Chemical Society, 2005
- Radical Amination with Sulfonyl Azides: A Powerful Method for the Formation of C-N BondsChemistry – A European Journal, 2004
- Click Chemistry: Diverse Chemical Function from a Few Good ReactionsAngewandte Chemie-International Edition, 2001
- Formation of Carbon−Nitrogen Bonds via a Novel Radical Azidation ProcessJournal of the American Chemical Society, 2000
- Azidyl Radical Reactivity. N6.bul.- as a Kinetic Probe for the Addition Reactions of Azidyl Radicals with OlefinsJournal of the American Chemical Society, 1995
- Surface-mediated reactions. 2. Addition of hydrazoic acid to alkenesThe Journal of Organic Chemistry, 1992
- Synthetic methods. 19. Lewis acid catalyzed conversion of alkenes and alcohols to azidesThe Journal of Organic Chemistry, 1984