Advanced Synthesis and Catalysis p. 1108 - 1116 (2019)
Update date:2022-08-05
Topics:
Ignatiuk, ?aneta A.
Janicki, Miko?aj J.
Góra, Robert W.
Konieczny, Krzysztof
Kowalczyk, Rafa?
Stereoselective addition of nitromethane to conjugated en-ynones was performed through the application of chiral squaramides. Three non-classical approaches to promote the addition reaction were tested, including activation of the nucleophile by inorganic base in a biphasic aqueous system, thermal activation, and ball-milling. Hydrogen-bonding catalysis was effective in all these methods, providing 1,4-addition products in high yields and stereoselectivities of up to 98% requiring 1–5 mol% of Cinchona alkaloid squaramide. (Figure presented.).
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