Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 28, Pages 4848-4853Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900716
Keywords
Asymmetric catalysis; Michael addition; Alkenes; Organocatalysis; Pyrrolidine; Catalyst design
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Funding
- National Natural Science Foundation of China [20672061, 2007AA05Z102]
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A new class of chiral pyrrolidine-pyridine-based organocatalysts, available from commercially available starting materials, have been synthesized and shown to be very effective catalysts for the asymmetric Michael addition reactions of cyclic/acyclic/aromatic ketones and an aldehyde with nitro olefins, giving excellent yields (up to 99%), diastereoselectivities (syn/anti = 99:1), and enantioselectivities (up to 99%). Based on the experimental results and ESI-MS analysis of the intermediates, the mode of activity of the organocatalyst with the substrate was deduced. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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