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Catalytic Direct Asymmetric Michael Reactions:  Taming Naked Aldehyde Donors

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posted on 23.10.2001, 00:00 by Juan M. Betancort, Carlos F. Barbas
Direct catalytic enantio- and diastereoselective Michael addition reactions of unmodified aldehydes to nitro olefins using (S)-2-(morpholinomethyl)pyrrolidine as a catalyst are described. The reactions proceed in good yield (up to 96%) in a highly syn-selective manner (up to 98:2) with enantioselectivities approaching 80%. The resulting γ-formyl nitro compounds are readily converted to chiral, nonracemic 3,4-disubstituted pyrrolidines.