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- Title
Gold-Catalyzed Tandem Hydroamination/Formal Aza-Diels-Alder Reaction of Homopropargyl Amino Esters: A Combined Computational and Experimental Mechanistic Study.
- Authors
Miró, Javier; Sánchez ‐ Roselló, María; González, Javier; del Pozo, Carlos; Fustero, Santos
- Abstract
A tandem gold-catalyzed hydroamination/formal aza-Diels-Alder reaction is described. This process, which employs quaternary homopropargyl amino ester substrates, leads to the formation of an intrincate tetracyclic framework and involves the generation of four bonds and five stereocenters in a highly diastereoselective manner. Theoretical calculations have allowed us to propose a suitable mechanistic rationalization for the tandem protocol. Additionally, by studying the influence of the ligands on the rate of the gold-catalyzed reactions, it was possible to establish optimum conditions in which to perform the process with a variety of substituents on the amino ester substrates. Notably, the asymmetric version of the tandem reaction was also evaluated.
- Subjects
GOLD catalysts; HYDROAMINATION; DIELS-Alder reaction; ESTERS; BIOCHEMICAL substrates; LIGANDS (Chemistry)
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 14, p5459
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201406224