Organocatalytic enantioselective Michael addition of β-diketones to β-nitrostyrene: the first Michael addition of dipivaloylmethane to an activated olefin.

The addition of a family of β-diketones to β-nitrostyrene was explored using a library of cinchona organocatalysts.A thiourea organocatalyst, under improved reaction conditions, is shown to be much more efficient at catalyzing this reaction than previously reported giving excellent yields and enantioselectivites (up to 95% yield and 97% ee).The same thiourea organocatalyst was employed in the first successful Michael addition of the sterically challenging dipivaloylmethane to β-nitrostyrene (99% ee).

Abstract licence: CC BY

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