4.8 Article

Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors

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ORGANIC LETTERS
卷 3, 期 23, 页码 3737-3740

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AMER CHEMICAL SOC
DOI: 10.1021/ol0167006

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  1. NCI NIH HHS [CA27489] Funding Source: Medline

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[GRAPHICS] 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 enantloselectivities approaching 80%. The resulting gamma -formyl nitro compounds are readily converted to chiral, nonracemic 3,4-disubstituted pyrrolidines.

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