Journal
SYNLETT
Volume 34, Issue 6, Pages 663-666Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1938-1243
Keywords
spiropyrazolones; oxa-Michael reaction; organocatalysis; asymmetric catalysis; enantioselectivity; cascade reaction
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An organocatalytic asymmetric oxa-Michael-Michael reaction was developed for the synthesis of spirotetrahydropyranopyrazolones. By utilizing a quinine-derived squaramide catalyst, the reaction achieved moderate yields, excellent diastereomeric ratios, and high to excellent enantioselectivities under mild reaction conditions.
An organocatalytic asymmetric oxa-Michael-Michael reaction of 3-aryl-2-nitroprop-2-enols with alkylidene pyrazolones has been developed. This report describes the first use of a 3-aryl-2-nitroprop-2-enol as an O-nucleophile in enantioselective catalysis. With 10 mol% of a quinine-derived squaramide catalyst, a variety of spirotetrahydropyranopyrazolones were obtained in moderate yields, excellent diastereomeric ratios, and high to excellent enantioselectivities under mild reaction conditions.
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