ArticleOrganic letters2015
Highly Diastereoselective Michael Reactions Using β-Nitrocarbonyl Nucleophiles.
Article in Organic letters, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- A General Method forOrganic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2025Article
- Photoredox-Nickel Dual-CatalyzedJournal of the American Chemical Society · 2023Article
- Nickel-Catalyzed Asymmetric C-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides.Journal of the American Chemical Society · 2019Article
- Trifluoromethylation of Secondary Nitroalkanes.Organic letters · 2017Article
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Authors and funding
3 authors.
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Abstract
We have discovered a highly diastereoselective Michael reaction of α-substituted, β-nitrocarbonyl compounds to deliver highly functionalized stereodiads containing fully substituted nitrogen-bearing centers. Good to excellent yields and diastereoselectivities are observed. This transformation is tolerant of various types of carbonyl groups on the nucleophilic partner, as well as a range of unsaturated electrophiles. Mechanistic investigations are consistent with internal hydrogen bonding in the nitroalkane tautomer as the major factor in the control of diastereoselectivity in these transformations.
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