ORGN 89 |
Novel metal-mediated approaches for the rapid assembly of nitrogen heterocycles
| Richard H. Blaauw1, Sape S. Kinderman2, Henk Hiemstra2, Bart C.J. van Esseveldt3, and Floris P.J.T. Rutjes3. (1) Chiralix B.V, Toernooiveld 100, 6525 EC Nijmegen, Netherlands, (2) Organic Chemistry, University of Amsterdam, Amsterdam, Netherlands, (3) Department of Organic Chemistry, University of Nijmegen, Toernooiveld 1, Nijmegen, 6525 ED, Netherlands |
Efficient sequences for the construction of multifunctional nitrogen heterocyclic scaffolds will be detailed. A first approach consists of the formation of reactive acetals, followed by different types of cyclization reactions. More specifically, palladium-catalyzed coupling of alkoxy allenes to carbamates or sulfonamides provides stable N,O-acetals, that can be efficiently elaborated to highly functionalized heterocycles. A second approach involves the use of palladium and silver catalysts in the cyclization of acetylenic amino acids. By choosing either catalyst, both 5-arylprolines as well as isotryptophans can be efficiently obtained. |
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New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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