Synthesis of Allenamides by Copper-Catalyzed Coupling of Allenyl Halides with Amides, Carbamates, and Ureas
- 26 April 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (11) , 2117-2120
- https://doi.org/10.1021/ol050395x
Abstract
A variety of N-substituted allenes have been synthesized by the copper-catalyzed coupling reaction between allenyl halides and amides, carbamates, and ureas. The reactions proceed in good to excellent yield using 7 mol % copper thiophenecarboxylate and 15 mol % of a diamine catalyst.Keywords
This publication has 35 references indexed in Scilit:
- Chiral Lewis Acid-Catalyzed Highly Enantioselective [4 + 3] Cycloaddition Reactions of Nitrogen-Stabilized Oxyallyl Cations Derived from AllenamidesJournal of the American Chemical Society, 2004
- Synthesis of 1-Deoxy-d-galactohomonojirimycin via Enantiomerically Pure AllenylstannanesThe Journal of Organic Chemistry, 2003
- Syntheses and Reactions of Optically Active α-AminoallenylstannanesThe Journal of Organic Chemistry, 2003
- A Highly cis-Selective Synthesis of 2-Ethynylaziridines by Intramolecular Amination of Chiral Bromoallenes: Improvement of Stereoselectivity Based on the Computational InvestigationJournal of the American Chemical Society, 2002
- Synthesis of spiro- and fused heterocycles by palladium catalysed carbo- and heteroannulation cascades of allenesChemical Communications, 2001
- Palladium-catalysed cyclisation–amination of allenes-effect of base on regioselectivity of formation of allylic aminesJournal of the Chemical Society, Chemical Communications, 1995
- 1,3-Diastereocontrol with bromoallenes. Synthesis of enantiomerically pure β-branched α-amino acidsTetrahedron Letters, 1994
- Palladium-Catalyzed Coupling of Stannyl Allenes With Aryl IodidesSynthetic Communications, 1994
- Synthesis and absolute configurations of halogenoallenesThe Journal of Organic Chemistry, 1985
- Studies dealing with the aza Claisen rearrangement of 2-allyloxy-substituted oxazolesThe Journal of Organic Chemistry, 1984