4.8 Article

Asymmetric Michael Addition of γ,γ-Disubstituted α,β-Unsaturated Aldehydes to Nitroolefins via Dienamine Catalysis

Journal

ORGANIC LETTERS
Volume 11, Issue 20, Pages 4660-4663

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol901939b

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Funding

  1. National Natural Science Foundation of China [20772084]

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The first chemo- and alpha-regioselective asymmetric Michael addition of gamma,gamma-disubstituted alpha,beta-unsaturated aldehydes to nitroolefins has been presented in excellent diastereo- and enantioselectivities (dr up to >99:1, 93-96% ee) via dienamine catalysis. The Michael adducts have been efficiently converted to a number of optically pure cyclic frameworks with versatile scaffold diversity.

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