AI Article Synopsis
- A new method for the intramolecular Stetter reaction has been created, utilizing aromatic and aliphatic aldehydes with various Michael acceptors for high enantioselectivity.
- Two specific triazolium compounds were found to effectively catalyze this reaction, showing wide applicability across different types of aldehydes and linkers.
- Reaction efficiency remains high, even when catalyst loading is reduced to 3 mol %, allowing for versatile substrate combinations without sacrificing performance.
Article Abstract
A highly enantioselective intramolecular Stetter reaction of aromatic and aliphatic aldehydes tethered to different Michael acceptors has been developed. Two triazolium scaffolds have been identified that catalyze the intramolecular Stetter reaction with good reactivity and enantioselectivity. The substrate scope has been examined and found to be broad; both electron-rich and -poor aromatic aldehydes undergo cyclization in high yield and enantioselectivity. The tether can include oxygen, sulfur, nitrogen, and carbon linkers with no detrimental effects. In addition, the incorporation of various tethered Michael acceptors includes amides, esters, thioesters, ketones, aldehydes, and nitriles. The catalyst loading may be reduced to 3 mol % without significantly affecting the reactivity or selectivity of the reaction.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4222522 | PMC |
| http://dx.doi.org/10.1021/jo702313f | DOI Listing |
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