Answers are grounded in this paper and cite their sources.
Demonstrates a novel reductive nitro-Mannich cyclization yielding alkaloids, highlighting its significant application in natural product synthesis.
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.
No takes yet. Share an insight, caveat, or question.
Gregory et al. (2014) studied this question.
Synapse has enriched 10 related papers. Consider them for comparative context: