Catalytic Asymmetric Allylic and Homoallylic Diamination of Terminal Olefins via Formal C−H Activation
- 13 June 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (27), 8590-8591
- https://doi.org/10.1021/ja8027394
Abstract
This paper describes a catalytic asymmetric diamination process for terminal olefins at allylic and homoallylic carbons via formal C−H activation using di-tert-butyldiaziridinone as nitrogen source with a catalyst generated from Pd2(dba)3 and chiral phosphorus amidite ligand. A wide variety of readily available terminal olefins can be effectively diaminated in good yields with high regio-, diastereo-, and enantioselectivities.Keywords
This publication has 34 references indexed in Scilit:
- Vicinal Diamino Functionalities as Privileged Structural Elements in Biologically Active Compounds and Exploitation of their Synthetic ChemistryChemical Biology & Drug Design, 2006
- Copper(II) Acetate Promoted Intramolecular Diamination of Unactivated OlefinsJournal of the American Chemical Society, 2005
- Electronic Effects in Olefin Oxidation by Imidoosmium(VIII) CompoundsEuropean Journal of Organic Chemistry, 2004
- The Chemistry of Vicinal DiaminesAngewandte Chemie International Edition, 1998
- Conversion of alkenes to 1,2-diazides and 1,2-diaminesThe Journal of Organic Chemistry, 1985
- A new method for 1,2-diamination of alkenes using cyclopentadienylnitrosylcobalt dimer/NO/LiAlH4Journal of the American Chemical Society, 1980
- Mercury(II) Oxide/Tetrafluoroboric Acid - A New Reagent in Organic Synthesis; A Convenient Diamination of OlefinsSynthesis, 1979
- Stereospecific palladium-promoted vicinal diamination of olefinsTetrahedron Letters, 1978
- Synthesis of dioxobis(tert-alkylimido)osmium(VIII) and oxotris(tert-alkylimido)osmium(VIII) complexes. Stereospecific vicinal diamination of olefinsJournal of the American Chemical Society, 1977
- The Addition of Aromatic Amines to Alkenes in the Presence of Thallium(III) AcetateSynthesis, 1974