ArticleAngewandte Chemie (International ed. in English)2013
Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.
Article in Angewandte Chemie (International ed. in English), 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Stereoselective, borane-catalysed synthesis ofChemical science · 2026Article
- Atom-economic and stereoselective catalytic synthesis of fully substituted enol esters/carbonates of amides in acyclic systems enabled by boron Lewis acid catalysis.Chemical science · 2023Article
- Diastereoselective, Catalytic Access to Cross-Aldol Products Directly from Esters and Lactones.Angewandte Chemie (International ed. in English) · 2022Article
- Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations.Catalysts (Basel, Switzerland) · 2021Article
- Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.Chemical reviews · 2020Review
- A borane-mediated palladium-catalyzed reductive allylic alkylation of α,β-unsaturated carbonyl compounds.Chemical science · 2020Article
- Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.Journal of the American Chemical Society · 2017Article
- Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres.Chemical science · 2017Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
On all fours: The title reaction with (Ipc)2 BH provides tetrasubstituted enolborinates which undergo aldol reactions with aldehydes to form products with all-carbon quaternary centers with exceptional diastereo- and enantioselectivity. A change to the substitution pattern of the starting amide leads to either diastereomer of the α-methyl-α-ethyl-β-hydroxy carboxamide (1 or 2).
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Registered trials
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