ArticleJournal of the American Chemical Society2011
Convergent and stereodivergent synthesis of complex 1-aza-7-oxabicyclo[2.2.1]heptanes.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Modern applications of low-valent early transition metals in synthesis and catalysis.Nature reviews. Chemistry · 2019Article
- Synthesis of Highly Oxygenated Carbocycles by Stereoselective Coupling of Alkynes to 1,3- and 1,4-Dicarbonyl Systems.Journal of the American Chemical Society · 2017Article
- Reaction design, discovery, and development as a foundation to function-oriented synthesis.Accounts of chemical research · 2015Article
- Stereochemical lability of azatitanacyclopropanes: dynamic kinetic resolution in reductive cross-coupling reactions with allylic alcohols.Chemical communications (Cambridge, England) · 2013Article
- Catalytic Z-selective cross-metathesis with secondary silyl- and benzyl-protected allylic ethers: mechanistic aspects and applications to natural product synthesis.Angewandte Chemie (International ed. in English) · 2013Article
- Synthesis of alkaloid (-)-205B via stereoselective reductive cross-coupling and intramolecular [3+2] cycloaddition.Journal of the American Chemical Society · 2012Article
- Three-component coupling sequence for the regiospecific synthesis of substituted pyridines.Journal of the American Chemical Society · 2012Article
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2 authors.
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Abstract
A convergent and stereodivergent pathway to highly substituted 1-aza-7-oxabicyclo[2.2.1]heptanes is described. It begins with a coupling reaction involving allylic alcohol, aldehyde, and LiHMDS to produce stereodefined primary homoallylic amines. Subsequent N-oxidation and condensation with formaldehyde or glyoxylate defines a convenient entry to densely functionalized homoallylic nitrones whose intramolecular annulation can be controlled to deliver one of two distinct heterocyclic skeletons, each with ≥20:1 stereoselection. Control of the stereochemistry in these reactions results from both control of the nitrone geometry and selective partitioning of the reaction pathway between direct [3 + 2] cycloaddition and tandem [3,3] rearrangement/[3 + 2] cycloaddition.
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