Catalytic Direct Asymmetric Michael Reactions:  Taming Naked Aldehyde Donors

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 enantioselect...

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Bibliographic Details
Published in:Organic letters 2001-11, Vol.3 (23), p.3737-3740
Main Authors: Betancort, Juan M, Barbas, Carlos F
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Alkenes - chemistry
Catalysis
Indicators and Reagents
Kinetics
Morpholines - chemical synthesis
Pyrroles - chemical synthesis
Pyrrolidines - chemical synthesis
Stereoisomerism
Temperature
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0167006