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- Title
Iridium-Catalyzed Reductive Nitro-Mannich Cyclization.
- Authors
Gregory, Alex W.; Chambers, Alan; Hawkins, Alison; Jakubec, Pavol; Dixon, Darren J.
- Abstract
A new chemoselective reductive nitro-Mannich cyclization reaction sequence of nitroalkyl-tethered lactams has been developed. Relying on the rapid and chemoselective iridium(I)-catalyzed reduction of lactams to the corresponding enamine, subsequent nitro-Mannich cyclization of tethered nitroalkyl functionality provides direct access to important alkaloid natural-product-like structures in yields up to 81% and in diastereoselectivities that are typically good to excellent. An in-depth understanding of the reaction mechanism has been gained through NMR studies and characterization of reaction intermediates. The new methodology has been applied to the total synthesis of (±)-epi-epiquinamide in four steps.
- Subjects
IRIDIUM catalysts; MANNICH reaction; RING formation (Chemistry); NUCLEAR magnetic resonance; CHEMOSELECTIVITY
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 1, p111
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201405256