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.
Key Words
spiropyrazolones - oxa-Michael reaction - organocatalysis - asymmetric catalysis -
enantioselectivity - cascade reaction