ArticleOrganic letters2012
Divergent stereocontrol of acid catalyzed intramolecular aldol reactions of 2,3,7-triketoesters: synthesis of highly functionalized cyclopentanones.
Article in Organic letters, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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Who cites it
9 citing papers in PubMed, 53 citations in OpenAlex.
- B(CRSC advances · 2022Article
- [3+2] Cycloaddition of alkyl aldehydes and alkynes enabled by photoinduced hydrogen atom transfer.Nature communications · 2022Article
- Synthesis of the ABC Ring of Calyciphylline A-Type Alkaloids by a Stereocontrolled Aldol Cyclization: Formal Synthesis of (±)-Himalensine A.The Journal of organic chemistry · 2022Article
- Vicinal ketoesters - key intermediates in the total synthesis of natural products.Beilstein journal of organic chemistry · 2022Review
- Iron-Catalyzed Synthesis of Tetrahydronaphthalenes via 3,4-Dihydro-2H-pyran Intermediates.Organic letters · 2018Article
- Cycloaddition reactions of enoldiazo compounds.Chemical Society reviews · 2017Review
- Functionalizing the γ-Position of α-Diazo-β-ketoesters.Tetrahedron letters · 2016Article
- Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.Chemical communications (Cambridge, England) · 2016Article
- Direct access to 6/5/7/5- and 6/7/5/5-fused tetracyclic triterpenoids via divergent transannular aldol reaction of lanosterol-derived diketone.The Journal of organic chemistry · 2013Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The intramolecular acid catalyzed aldol cyclization of 2,3,7-triketoesters formed from ζ-keto-α-diazo-β-ketoesters provides highly functionalized cyclopentanones with good diastereoselectivity in high overall yields via kinetically controlled and stereodivergent catalytic processes. Lewis acid catalysis gives high selectivity for the 1,2-anti tetrasubstituted cyclopentanones, whereas Brønsted acid catalysis produces the corresponding 1,2-syn diastereomer.
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Registered trials
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