Direct Electrophilic Diamination of Functionalized Alkenes without the Use of Any Metal Catalysts
- 13 June 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (14) , 5742-5745
- https://doi.org/10.1021/jo030098a
Abstract
A new direct electrophilic diamination reaction of α,β-unsaturated ketones and esters has been established without the use of any metal catalysts. Three types of nitriles (CH3CN, CH3CH2CN, and CH3CH2CH2CN) were employed as nucleophilic nitrogen sources. A new mechanism has also been proposed to explain the resulting regio- and stereoselectivity.Keywords
This publication has 29 references indexed in Scilit:
- A First Asymmetric Diamination of OlefinsSynlett, 2003
- Electrophilic Diamination of Alkenes by Using FeCl3−PPh3 Complex as the CatalystThe Journal of Organic Chemistry, 2002
- Practical and Efficient Synthesis of C2 Symmetrical Diamines with Zn/Me3SiClSynlett, 1998
- β‐Silyl Diorganozinc Compounds—A New Class of Useful Zinc ReagentsAngewandte Chemie International Edition in English, 1997
- Synthesis of Nα, Nβ-alkylated Diaminopropionic Acid AnalogsTetrahedron Letters, 1995
- A practical, highly enantioselective synthesis of the taxol side chain via asymmetric catalysis.The Journal of Organic Chemistry, 1992
- Donor Ligand Effect in Asymmetric Epoxidation of Unfunctionalized Olefins with Chiral Salen ComplexesSynlett, 1991
- Mercury(II) Oxide/Tetrafluoroboric Acid; A Convenient Reagent for the Hydroxy(alkoxy)-phenylamination of AlkenesSynthesis, 1981
- Enantioface-differentiating (asymmetric) addition of alkyllithium and dialkylmagnesium to aldehydes by using (2S,2'S)-2-hydroxymethyl-1-[(1-alkylpyrrolidin-2-yl)methyl]pyrrolidines as chiral ligandsJournal of the American Chemical Society, 1979
- 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