Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 6, Pages 2033-2040Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo702313f
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Funding
- NIGMS NIH HHS [R01 GM072586, GM72586] Funding Source: Medline
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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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