Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 5, Pages 1108-1116Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201801498
Keywords
hydrogen-bonding; Michael addition; thermal activation; ball-milling; organocatalysis
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Funding
- National Science Center, Poland [2016/22/E/ST5/00046]
- Wroclaw Centre of Networking and Super-computing (WCSS)
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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 1-5mol% of Cinchona alkaloid squaramide.
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