Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 14, Pages 2492-2499Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600316
Keywords
Asymmetric synthesis; Organocatalysis; Domino reactions; Michael addition; Spiro compounds; Nitrogen heterocycles
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Funding
- National Natural Science Foundation of China (NSFC) [21272024]
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A new method was developed to rapidly generate a series of spiro-pyrrolidine-pyrazolones by using a squaramide-catalyzed cascade aza-Michael/Michael addition of either tosyl-aminomethyl enones or enoates to unsaturated pyrazolones. This tandem reaction sequence proceeded well by using 5 mol-% of a chiral bifunctional tertiary amine squaramide catalyst to afford the desired products in good to excellent yields (up to 98 %) with excellent diastereoselectivities [up to >20:1 diastereomeric ratio (dr)] and high to excellent enantioselectivities (up to 98 % ee).
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