ArticleNature communications2024
Palladium-catalyzed cascade of aza-Wacker and Povarov reactions of aryl amines and 1,6-dienes for hexahydro-cyclopenta[b]quinoline framework.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Access to Fused Indolines with a QuaternaryOrganic letters · 2026Article
- Traditional and Sustainable Methods for the Synthesis of Quinoline Derivatives as Anticancer Agents (2019-Present): A Comprehensive Review.Anti-cancer agents in medicinal chemistry · 2026Review
- Development of a Highly Selective Synthesis of 4-Substituted Tetrahydroquinolines: Substrate Scope and Mechanistic Study.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
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Authors and funding
4 authors.
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Abstract
Palladium catalyzed tandem reaction represents a one-pot synthetic approach to efficiently synthesize complex functionalized molecules while reducing synthetic steps, aligning with the principles of green chemistry. However, achieving a direct cascade of the aza-Wacker and Povarov reactions in one-pot synthesis presents a challenge due to substrate compatibility issues between the two reactions. In this work, we describe an aza-Wacker/Povarov reaction employing a highly electrophilic palladium catalyst, which effectively converts anilines and 1,6-dienes into hexahydro-cyclopenta[b]quinolines. The optimized conditions yield up to 79%, with a diastereoselectivity > 20:1. Substrate range testing reveals compatibility with various sensitive functional groups, and successful late-stage modifications are performed on several natural products and drug molecules, demonstrating the versatility and practicality of the method. Additionally, a preliminary investigation into the reaction mechanism suggests an aza-Wacker process followed by a Povarov process.
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